3-Amino-1,2-propanediol → HCID 11614399, compound
Reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]([NH:21][C:22]3[N:27]=[C:26]([C:28]4[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=4)[CH:25]=[CH:24][N:23]=3)[CH:15]=2)=[O:12])[N:7]([C:34]2[CH:35]=[C:36]([CH2:40][C:41](OCC)=[O:42])[CH:37]=[CH:38][CH:39]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:46][CH2:47][CH:48]([OH:51])[CH2:49][OH:50]>>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]([NH:21][C:22]3[N:27]=[C:26]([C:28]4[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=4)[CH:25]=[CH:24][N:23]=3)[CH:15]=2)=[O:12])[N:7]([C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([CH2:40][C:41]([NH:46][CH2:47][CH:48]([OH:51])[CH2:49][OH:50])=[O:42])[CH:35]=2)[N:6]=1)([CH3:2])([CH3:3])[CH3:4]Participants
Procedure
Using the same method as for Example 21, ethyl 2-(3-(3-t-butyl-5-(3-(4-methyl-3-(4-(pyridin-3-yl)pyrimidin-2-ylamino)phenyl)ureido)-1H-pyrazol-1-yl)phenyl)acetate (137 mg, 0.23 mmol) and 1-amino-2,3-dihydroxypropane (49 mg, 0.54 mmol) were combined to yield 1-(3-t-butyl-1-(3-(2-(2,3-dihydroxypropylamino)-2-oxoethyl)phenyl)-1H-pyrazol-5-yl)-3-(4-methyl-3-(4-(pyridin-3-yl)pyrimidin-2-ylamino)phenyl)urea (81 mg, 69% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.29 (dd, J=2.2, and 0.8 Hz, 1H), 8.95 (s, 1H), 8.86 (s, 1H), 8.69 (dd, J=4.8, and 1.6 Hz, 1H), 8.51-8.47 (m, 2H), 8.38 (s, 1H), 8.10 (brt, J=5.8 Hz, 1H), 7.83 (d, J=1.6 Hz, 1H), 7.51 (ddd, J=8.4, 4.7, and 0.8 Hz, 1H), 7.47-7.42 (m, 3H), 7.36 (m, 1H), 7.31 (brd, J=7.6 Hz, 1H), 7.11 (d, J=8.5 Hz, 1H), 7.05 (dd, J=8.5, and 2.1 Hz, 1H), 6.41 (s, 1H), 4.76 (d, J=4.8 Hz, 1H), 4.51 (t, J=5.8 Hz, 1H), 3.53 (s, 2H), 3.48 (m, 1H), 3.30-3.18 (m, 3H), 2.96 (m, 1H), 2.19 (s, 3H), 1.27 (s, 9H); MS (ESI) m/z: 650.3 (M+H+).
Sources & evidence
- ORD record
- ord-86ee2131618944a0b2cb666f72738e56
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08163756B2
Reaction notes
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