(R)-1-(7-Amino-8-methoxy-1,2,4,5-tetrahydro-3-benzazepin-3-yl)-propan-2-ol → N-Cyclopropyl-3-{2-[3-((R)-2-hydroxy-propyl)-8-methoxy-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamino]-pyrrolo[2,1-f][1,2,4]triazin-7-yl}benzenesulfonamide

HRID 1262075Notes

Reaction equation

HRID 1262075 reaction equation
[CH:1]1([NH:4][S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]3[N:22]4[C:17]([CH:18]=[N:19][C:20](O)=[N:21]4)=[CH:16][CH:15]=3)[CH:9]=2)(=[O:7])=[O:6])[CH2:3][CH2:2]1.[NH2:24][C:25]1[C:39]([O:40][CH3:41])=[CH:38][C:28]2[CH2:29][CH2:30][N:31]([CH2:34][C@H:35]([OH:37])[CH3:36])[CH2:32][CH2:33][C:27]=2[CH:26]=1>>[CH:1]1([NH:4][S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]3[N:22]4[C:17]([CH:18]=[N:19][C:20]([NH:24][C:25]5[C:39]([O:40][CH3:41])=[CH:38][C:28]6[CH2:29][CH2:30][N:31]([CH2:34][C@H:35]([OH:37])[CH3:36])[CH2:32][CH2:33][C:27]=6[CH:26]=5)=[N:21]4)=[CH:16][CH:15]=3)[CH:9]=2)(=[O:6])=[O:7])[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 66711392(R)-1-(7-Amino-8-methoxy-1,2,4,5-tetrahydro-3-benzazepin-3-yl)-propan-2-olHCID 178527450HCID 178527450, compound

Product 1

HCID 66711805N-Cyclopropyl-3-{2-[3-((R)-2-hydroxy-propyl)-8-methoxy-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamino]-pyrrolo[2,1-f][1,2,4]triazin-7-yl}benzenesulfonamide

Procedure

This compound as a yellow solid, was prepared following the same procedure as described for the synthesis of Example 522 by coupling N-Cyclopropyl-3-(2-hydroxy-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-benzenesulfonamide and (R)-1-(7-Amino-8-methoxy-1,2,4,5-tetrahydro-3-benzazepin-3-yl)-propan-2-ol. MP>150° C. (decomp.). LCMS (E/I+) 563.14 (M+H). 1H NMR (DMSO-d6) δ 9.00 (s, 1H), 8.60 (d, 1H, J=6.50 Hz), 8.20 (s, 1H), 7.95 (s, 1H), 7.85 (m, 2H), 7.70 (t, 1H, J=6.50 Hz), 7.20 (d, 1H, J=6.00 Hz), 7.00 (d, 1H, J=6.00 Hz), 6.80 (s, 1H), 4.30 (broad, 1H), 3.80 (s, 3H), 3.70 (broad, 1H), 2.80 (broad, 2H), 2.70 (broad, 2H), 2.60 (broad, 4H), 2.40 (broad, 2H), 2.10 (broad, 1H), 1.20 (broad, 1H), 1.10 (d, 3H, J=6.00 Hz), 0.50 (broad, 2H), 0.40 (broad, 2H).

Workup

  1. customas described for the synthesis of Example 522

Sources & evidence

ORD record
ord-d987b6d1e86d436f8453b072388e8049
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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