2,2-Dimethylpropanethioamide → HCID 57990078, compound

HRID 590230Notes

Reaction equation

HRID 590230 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]([C:11]2[C:12]([F:25])=[C:13]([NH:18][C:19](=[O:24])[O:20][CH2:21][CH:22]=[CH2:23])[CH:14]=[CH:15][C:16]=2[F:17])=O)[CH:5]=[CH:4][N:3]=1.[CH3:26][C:27]([CH3:32])([CH3:31])[C:28](=[S:30])[NH2:29]>>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[S:30][C:28]([C:27]([CH3:32])([CH3:31])[CH3:26])=[N:29][C:9]=2[C:11]2[C:12]([F:25])=[C:13]([NH:18][C:19](=[O:24])[O:20][CH2:21][CH:22]=[CH2:23])[CH:14]=[CH:15][C:16]=2[F:17])[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 30311302,2-DimethylpropanethioamideHCID 579899062-Propen-1-yl {3-[(2-chloro-4-pyrimidinyl)acetyl]-2,4-difluorophenyl}carbamate

Product 1

HCID 57990078HCID 57990078, compoundYield 17%

Procedure

Following a procedure analogous to the procedure described in Intermediate 6 using 2-propen-1-yl {3-[(2-chloro-4-pyrimidinyl)acetyl]-2,4-difluorophenyl}carbamate (10 g, 27.2 mmol) NBS (5.08 g, 28.6 mmol) and 2,2-dimethylpropanethioamide (3.51 g, 29.9 mmol) the title compound of Step A was obtained (2.15 g, 17% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.55 (br. s., 1H), 8.67 (d, J=5.3 Hz, 1H), 7.83 (d, J=6.0 Hz, 1H), 7.27 (t, J=8.9 Hz, 1H), 7.16 (d, J=5.3 Hz, 1H), 5.89-6.01 (m, 1H), 5.34 (d, J=17.2 Hz, 1H), 5.22 (d, J=10.4 Hz, 1H), 4.60 (d, J=5.3 Hz, 2H), 1.45 (s, 9H); MS (ESI): 464 [M+H]+.

Sources & evidence

ORD record
ord-7f7b2fba2a5948898a1cde1e00b06f80
Source dataset
uspto-grants-2016_01
Patent number
US09233956B2

Reaction notes

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