Diisopropylethylamine → HCID 58709958, compound

HRID 2375844Notes

Reaction equation

HRID 2375844 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([NH:10][C:11]3[C:12]4[CH:19]=[C:18]([C:20]5[CH2:21][CH2:22][N:23]([C:26]([N:28]6[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]6)=[O:27])[CH2:24][CH:25]=5)[NH:17][C:13]=4[N:14]=[CH:15][N:16]=3)[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.Br[CH2:35][CH:36]1[CH2:39][CH2:38][CH2:37]1.CCN(C(C)C)C(C)C>>[S:1]1[C:5]2[CH:6]=[C:7]([NH:10][C:11]3[C:12]4[CH:19]=[C:18]([C:20]5[CH2:21][CH2:22][N:23]([C:26]([N:28]6[CH2:29][CH2:30][N:31]([CH2:35][CH:36]7[CH2:39][CH2:38][CH2:37]7)[CH2:32][CH2:33]6)=[O:27])[CH2:24][CH:25]=5)[NH:17][C:13]=4[N:14]=[CH:15][N:16]=3)[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 2734658(Bromomethyl)cyclobutaneHCID 58710077HCID 58710077, compound

Product 1

HCID 58709958HCID 58709958, compound

Procedure

The reaction mixture derived from the preparation of {4-[4-(benzothiazol-6-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-3,6-dihydro-2H-pyridin-1-yl}-piperazin-1-ylmethanone (EXAMPLE 154) was reacted with (bromomethyl)cyclobutane (90 mg, 5 eq.) in the presence of DIPEA at 60° C. for 72 h before the mixture was purified by HPLC, giving the title compound as yellow powder. 1H NMR (400 MHz, DMSO-d6): δ=11.78 (s, 1H), 9.52 (s, 1H), 9.16 (s, 1H), 8.84 (d, 1H, J=2.0 Hz), 8.26 (s, 1H), 8.14 (s, 1H), 7.97 (d, 1H, J=8.9 Hz), 7.91 (s, 1H), 7.80 (dd, 1H, J=2.0 Hz & 8.9 Hz), 6.82 (d, 1H, J=1.7 Hz), 6.57 (br s, 1H), 3.94 (s, 2H), 3.46 (m, 4H), 3.36 (m, 4H), 3.18 (m, 4H), 2.54 (br s, 2H), 2.46 (m, 1H), 2.34 (m, 3H), 2.03 (m, 1H), 1.84 (m, 1H), 1.65 (m, 1H). LC/MS: m/z 529.17 (15) [MH+], tR=1.94 (ZQ2000, polar—5 min).

Workup

  1. customwas purified by HPLC

Sources & evidence

ORD record
ord-ebea3b9dede9474195689c4eccc125e7
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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