17-[3-(2-Isopropylaminothiazol-4-yl)-6-methoxyisoquinolin-1-yloxy]-13-methyl-2,14-dioxo-3,13,15-triaza-tricyclo[13.3.0.04,6]octadec-7-ene-4-carboxylic acid → N-[17-[3-(2-isopropylaminothiazol-4-yl)-6-methoxyisoquinolin-1-yloxy]-13-methyl-2,14-dioxo-3,13,15-triaza-tricyclo[13.3.0.04,6]octadec-7-ene-4-carbonyl](cyclopropyl)sulfonamide

HRID 905555Notes

Reaction equation

[CH:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([C:10]2[N:11]=[C:12]([O:22][CH:23]3[CH2:40][CH:39]4[N:25]([C:26](=[O:46])[N:27]([CH3:45])[CH2:28][CH2:29][CH2:30][CH2:31][CH:32]=[CH:33][CH:34]5[C:36]([C:42](O)=[O:43])([NH:37][C:38]4=[O:41])[CH2:35]5)[CH2:24]3)[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([O:20][CH3:21])=[CH:15][CH:14]=3)[N:9]=1)([CH3:3])[CH3:2].ClC1N=C(OC2CC3N(C(=O)N(C)CCCCC=CC4C(C([NH:82][S:83]([CH:86]5[CH2:88][CH2:87]5)(=[O:85])=[O:84])=O)(NC3=O)C4)C2)C2C(C=1)=CC(OC)=CC=2>>[CH:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([C:10]2[N:11]=[C:12]([O:22][CH:23]3[CH2:40][CH:39]4[N:25]([C:26](=[O:46])[N:27]([CH3:45])[CH2:28][CH2:29][CH2:30][CH2:31][CH:32]=[CH:33][CH:34]5[C:36]([C:42]([NH:82][S:83]([CH:86]6[CH2:88][CH2:87]6)(=[O:85])=[O:84])=[O:43])([NH:37][C:38]4=[O:41])[CH2:35]5)[CH2:24]3)[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([O:20][CH3:21])=[CH:15][CH:14]=3)[N:9]=1)([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 7667482417-[3-(2-Isopropylaminothiazol-4-yl)-6-methoxyisoquinolin-1-yloxy]-13-methyl-2,14-dioxo-3,13,15-triaza-tricyclo[13.3.0.04,6]octadec-7-ene-4-carboxylic acid

HCID 76674828N-[17-(3-chloro-6-methoxyisoquinolin-1-yloxy)-13-methyl-2,14-dioxo-3,13,15-triaza-tricyclo[13.3.0.04,6]octadec-7-ene-4-carbonyl](cyclopropyl) sulfonamide

Product 1

HCID 76674830N-[17-[3-(2-isopropylaminothiazol-4-yl)-6-methoxyisoquinolin-1-yloxy]-13-methyl-2,14-dioxo-3,13,15-triaza-tricyclo[13.3.0.04,6]octadec-7-ene-4-carbonyl](cyclopropyl)sulfonamide

Procedure

The title product 72 was prepared from 17-[3-(2-isopropylaminothiazol-4-yl)-6-methoxyisoquinolin-1-yloxy]-13-methyl-2,14-dioxo-3,13,15-triaza-tricyclo-[13.3.0.04,6]octadec-7-ene-4-carboxylic acid (71) following the same procedures described for the preparation of N-[17-(3-chloro-6-methoxyisoquinolin-1-yloxy)-13-methyl-2,14-dioxo-3,13,15-triaza-tricyclo[13.3.0.04,6]octadec-7-ene-4-carbonyl]-(cyclopropyl)sulfonamide (43, Example 11): m/z=752 (M+H)+. 1H NMR (CDCl3): 0.93-1.03 (m, 1H), 1.05-1.15 (m, 1H), 1.18-1.28 (m, 3H), 1.32 (d, J=6.6 Hz, 3H), 1.34 (d, J=6.6 Hz, 3H), 1.36-1.67 (m, 4H), 1.93-2.07 (m, 2H), 2.22-2.36 (m, 1H), 2.45-2.65 (m, 3H), 2.85 (s, 3H), 2.91-3.00 (m, 1H), 3.05-3.17 (m, 1H), 3.64-3.80 (m, 3H), 3.89 (s, 3H), 4.08 (dd, J=3.8 Hz, J=10.9 Hz, 1H), 4.78 (t, J=8.1 Hz, 1H), 5.15 (t, J=10.4 Hz, 1H), 5.21-5.36 (broad s, 1H), 5.73 (dd, J=8.1 Hz, J=18.4 Hz, 1H), 5.94-6.02 (m, 1H), 6.92-6.99 (broad s, 1H), 7.00-7.07 (m, 2H), 7.22 (s, 1H), 7.74 (s, 1H), 7.95 (d, J=8.6 Hz, 1H), 10.54-10.99 (broad s, 1H).

Sources & evidence

ORD record: ord-13b908490d7d4bcebe9cf0b6cfe5dd53
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012939B2

Reaction notes

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