2-Bromo-5-methyl-1,3-thiazole → HCID 178430629, compound

HRID 707401Notes

Reaction equation

HRID 707401 reaction equation
C(O[C:6](=O)[NH:7][C@H:8]1[CH2:11][C@H:10]([N:12]2[C:16]3=[N:17][CH:18]=[CH:19][CH:20]=[C:15]3[C:14]([CH3:22])([CH3:21])[C:13]2=[O:23])[CH2:9]1)(C)(C)C.BrC1[S:27][C:28]([CH3:31])=[CH:29][N:30]=1>>[CH3:22][C:14]1([CH3:21])[C:15]2[C:16](=[N:17][CH:18]=[CH:19][CH:20]=2)[N:12]([C@H:10]2[CH2:9][C@H:8]([NH:7][C:6]3[S:27][C:28]([CH3:31])=[CH:29][N:30]=3)[CH2:11]2)[C:13]1=[O:23]

Participants

3

Reactant 2

HCID 219061062-Bromo-5-methyl-1,3-thiazoleHCID 178454100HCID 178454100, compound2×

Product 1

HCID 178430629HCID 178430629, compound

Procedure

3,3-Dimethyl-1-(trans-3-((5-methylthiazol-2-yl)amino)cyclobutyl)-1H-pyrrolo[2,3-b]pyridin-2(3H)-one was prepared by Method B7 using starting materials 1-(trans-3-aminocyclobutyl)-3,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-2(3H)-one hydrochloride (intermediate 26, 0.100 g, 0.329 mmol) and 2-bromo-5-methylthiazole (0.0585 g, 0.329 mmol) at 120° C. for 192 h. M+1: 329.1. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.31 (s, 6 H) 2.23 (d, J=1.17 Hz, 3 H) 2.24-2.33 (m, 2 H) 3.16-3.27 (m, 2 H) 4.23-4.33 (m, 1 H) 5.14 (quin, J=8.41 Hz, 1 H) 6.71 (br. d, J=1.20 Hz, 1 H) 7.08 (dd, J=7.24, 5.28 Hz, 1 H) 7.76 (dd, J=7.24, 1.56 Hz, 1 H) 7.81 (d, J=6.26 Hz, 1 H) 8.21 (dd, J=5.18, 1.66 Hz, 1 H).

Workup

  1. customat 120° C.
  2. customfor 192 h

Sources & evidence

ORD record
ord-7b869c2ddefd439f84bf60e14e9b9a5c
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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