2-Amino-3-methoxy-5-methyl-8,9-dihydro-5H-7-oxa-5-aza-benzocyclohepten-6-one → HCID 66829824, compound

HRID 1687846Notes

Reaction equation

HRID 1687846 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=2)[O:12][CH2:13][C:14]#[N:15])[C:5]([Cl:19])=[CH:4][N:3]=1.[NH2:20][C:21]1[C:22]([O:34][CH3:35])=[CH:23][C:24]2[N:30]([CH3:31])[C:29](=[O:32])[O:28][CH2:27][CH2:26][C:25]=2[CH:33]=1>>[Cl:19][C:5]1[C:6]([NH:8][C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=2)[O:12][CH2:13][C:14]#[N:15])=[N:7][C:2]([NH:20][C:21]2[C:22]([O:34][CH3:35])=[CH:23][C:24]3[N:30]([CH3:31])[C:29](=[O:32])[O:28][CH2:27][CH2:26][C:25]=3[CH:33]=2)=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 672646482-Amino-3-methoxy-5-methyl-8,9-dihydro-5H-7-oxa-5-aza-benzocyclohepten-6-oneHCID 86633946[3-(2,5-Dichloropyrimidin-4-ylamino)-phenoxy]acetonitrile

Product 1

HCID 66829824HCID 66829824, compoundYield 50%

Procedure

In an analogous manner to Example 1503, the product was prepared from [3-(2,5-Dichloro-pyrimidin-4-ylamino)-phenoxy]-acetonitrile and 2-Amino-3-methoxy-5-methyl-8,9-dihydro-5H-7-oxa-5-aza-benzocyclohepten-6-one. Product isolated as a white solid (45 mg, 50%). mp: 227-229° C., MS (ESI+): 481 (M+H), 1H-NMR (CDCl3, 400 MHz) δ 8.91 (s, 1H), 8.15 (s, 1H), 7.96 (s, 1H), 7.73 (s, 1H), 7.37 (s, 1H), 7.35 (s, 1H), 7.30 (t, 1H), 6.99 (s, 1H), 6.82 (d, J=8 Hz, 1H), 5.11 (s, 2H), 4.28 (t, 2H), 3.83 (s, 3H), 3.28 (s, 3H), 2.71 (t, 2H).

Sources & evidence

ORD record
ord-adcc44f89b5a40d9bc1e899f2ac18763
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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