HCID 57853899, compound → HCID 66829750, compound

HRID 1041298Notes

Reaction equation

HRID 1041298 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:14][CH2:13][C:12](=[O:15])[C:11]3[N:7]([CH:8]=[CH:9][CH:10]=3)[C:6]=2[CH:16]=1.Cl[C:18]1[N:23]=[C:22]([NH:24][C:25]2[C:34]([F:35])=[CH:33][CH:32]=[CH:31][C:26]=2[C:27]([NH:29][CH3:30])=[O:28])[C:21]([Cl:36])=[CH:20][N:19]=1>>[Cl:36][C:21]1[C:22]([NH:24][C:25]2[C:34]([F:35])=[CH:33][CH:32]=[CH:31][C:26]=2[C:27]([NH:29][CH3:30])=[O:28])=[N:23][C:18]([NH:1][C:2]2[CH:3]=[CH:4][C:5]3[O:14][CH2:13][C:12](=[O:15])[C:11]4[N:7]([CH:8]=[CH:9][CH:10]=4)[C:6]=3[CH:16]=2)=[N:19][CH:20]=1

Participants

3

Reactant 2

HCID 57853899HCID 57853899, compoundHCID 717421912-(2,5-Dichloropyrimidin-4-ylamino)-3-fluoro-N-methyl-benzamide

Product 1

HCID 66829750HCID 66829750, compound

Procedure

2-[5-Chloro-2-(4-oxo-4,5-dihydro-6-oxa-10b-aza-benz[e]azulen-9-ylamino)-pyrimidin-4-ylamino]-3-fluoro-N-methyl-benzamide was prepared from 9-Amino-6-oxa-10b-aza-benz[e]azulen-4-one and 2-(2,5-Dichloro-pyrimidin-4-ylamino)-3-fluoro-N-methyl-benzamide in an analogous manner to Example 1223c. Product was obtained as a tan ppt. MP 223-225 (dec) LCMS 493.09 (M+H), HPLC purity 95%, 1H-NMR (DMSO-D6, 400 MHZ) Δ 9.56 (s, 1H), 9.48 (s, 1H), 8.52 (d, J=4.6 Hz, 1H), 8.23 (s, 1H), 7.68 (s, 1H), 7.43 (d, J=7.6 Hz, 1H), 7.34 (s, 1H), 7.17-7.10 (m, 2H), 7.08 (s, 1H), 6.53 (d, J=2.5H, 1H), 4.67 (s, 2H), 2.73 (d, J=4.5 Hz, 3H).

Workup

  1. customProduct was obtained as a tan ppt

Sources & evidence

ORD record
ord-4f0f7e8c28c548089d633103c6cde7db
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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