2-chloro-N,N-dimethylacetamide → HCID 59612344, compound

HRID 1890093Notes

Reaction equation

HRID 1890093 reaction equation
[F:1][CH:2]([F:33])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[C:12]1[C:13]2[N:14]([N:18]=[C:19]([NH:21][C:22]3[CH:32]=[CH:31][C:25]4[CH2:26][CH2:27][NH:28][CH2:29][CH2:30][C:24]=4[CH:23]=3)[N:20]=2)[CH:15]=[CH:16][CH:17]=1.Cl[CH2:35][C:36]([N:38]([CH3:40])[CH3:39])=[O:37]>>[F:33][CH:2]([F:1])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[C:12]1[C:13]2[N:14]([N:18]=[C:19]([NH:21][C:22]3[CH:32]=[CH:31][C:25]4[CH2:26][CH2:27][N:28]([CH2:35][C:36]([N:38]([CH3:40])[CH3:39])=[O:37])[CH2:29][CH2:30][C:24]=4[CH:23]=3)[N:20]=2)[CH:15]=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 758862-chloro-N,N-dimethylacetamideHCID 86648369HCID 86648369, compound

Product 1

HCID 59612344HCID 59612344, compound

Procedure

2-(7-{8-[2-(2,2-Difluoro-ethoxy)-5-fluoro-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino}-1,2,4,5-tetrahydro-3-benzazepin-3-yl)-N,N-dimethyl-acetamide was prepared from {8-[2-(2,2-difluoro-ethoxy)-5-fluoro-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)-amine (0.097 g, 0.210 mmol) and 2-chloro-N,N-dimethyl-acetamide (0.033 mL, 0.321 mmol) in a manner analogous to Example 313 to give product (0.045 g, 39%). MP=218° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.53 (s, 1H), 8.78 (d, 1H), 7.62 (m, 2H), 7.40 (m, 2H), 7.29 (m, 2H), 7.00 (m, 2H), 6.23 (br m, 1H), 4.35 (m, 2H), 3.22 (s, 2H), 3.05 (s, 3H), 2.80 (br m, 7H), 2.60 (m, 4H). MS=539 (MH)+.

Sources & evidence

ORD record
ord-4e4bd34a9b374a86a349b0240d6e5796
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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