2-chloro-N,N-dimethylacetamide → HCID 59612352, compound

HRID 1890083Notes

Reaction equation

HRID 1890083 reaction equation
[F:1][CH:2]([F:32])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[C:12]2[N:13]([N:17]=[C:18]([NH:20][C:21]3[CH:31]=[CH:30][C:24]4[CH2:25][CH2:26][NH:27][CH2:28][CH2:29][C:23]=4[CH:22]=3)[N:19]=2)[CH:14]=[CH:15][CH:16]=1.Cl[CH2:34][C:35]([N:37]([CH3:39])[CH3:38])=[O:36]>>[F:32][CH:2]([F:1])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[C:12]2[N:13]([N:17]=[C:18]([NH:20][C:21]3[CH:31]=[CH:30][C:24]4[CH2:25][CH2:26][N:27]([CH2:34][C:35]([N:37]([CH3:39])[CH3:38])=[O:36])[CH2:28][CH2:29][C:23]=4[CH:22]=3)[N:19]=2)[CH:14]=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 758862-chloro-N,N-dimethylacetamideHCID 59612399HCID 59612399, compound

Product 1

HCID 59612352HCID 59612352, compound

Procedure

2-(7-{8-[2-(2,2-Difluoro-ethoxy)-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)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)-amine (0.100 g, 0.230 mmol) and 2-chloro-N,N-dimethyl-acetamide (0.035 mL, 0.344 mmol) in a manner analogous to Example 313 to give product (0.045 g, 38%). MP=213-215° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.49 (s, 1H), 8.77 (d, 1H), 7.65 (m, 2H), 7.40 (m, 2H), 7.35 (s, 1H), 7.25 (m, 1H), 7.15 (m, 1H), 7.05 (m, 1H), 6.98 (m, 1H), 6.22 (br m, 1H), 4.35 (m, 2H), 3.22 (s, 2H), 3.05 (s, 3H), 2.75 (m, 7H), 2.55 (m, 4H). MS=521 (MH)+.

Sources & evidence

ORD record
ord-4d9e237d78814c8790c870cb2ca89f46
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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