2-Bromo-4-methyl-1,3-thiazole → HCID 178431963, compound

HRID 707399Notes

Reaction equation

HRID 707399 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][CH:28]=[C:29]([CH3:31])[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][CH:28]=[C:29]([CH3:31])[N:30]=3)[CH2:11]2)[C:13]1=[O:23]

Participants

3

Reactant 2

HCID 5515412-Bromo-4-methyl-1,3-thiazoleHCID 178454100HCID 178454100, compound2×

Product 1

HCID 178431963HCID 178431963, compound

Procedure

3,3-Dimethyl-1-(trans-3-((4-methylthiazol-2-yl)amino)cyclobutyl)-1 h-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-4-methylthiazole (0.0585 g, 0.329 mmol) at 120° C. for 96 h. M+1: 329.1. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.38 (s, 6 H) 2.25 (s, 3 H) 2.33-2.42 (m, 2 H) 3.38-3.49 (m, 2 H) 4.35 (br. s., 1 H) 5.27 (quin, J=8.56 Hz, 1 H) 5.60 (br. s., 1 H) 6.09 (s, 1 H) 6.96 (t, J=6.16 Hz, 1 H) 7.43 (d, J=6.85 Hz, 1 H) 8.17 (d, J=5.30 Hz, 1 H).

Workup

  1. customat 120° C.
  2. customfor 96 h

Sources & evidence

ORD record
ord-1baad26a557b4b08ba333192452325f5
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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