Formamide → HCID 9824224, compound

HRID 1070531Notes

Reaction equation

[CH:1]([NH2:3])=[O:2].[Br:4][C:5]1[CH:6]=[C:7]([CH:27]=[CH:28][CH:29]=1)[NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([CH2:19][C:20]2[CH:25]=[CH:24][N:23]=[C:22](C)[CH:21]=2)=[N:11][N:10]=1>>[Br:4][C:5]1[CH:6]=[C:7]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([CH2:19][C:20]3[CH:21]=[CH:22][N:23]=[C:24]([C:1]([NH2:3])=[O:2])[CH:25]=3)=[N:11][N:10]=2)[CH:27]=[CH:28][CH:29]=1

Participants

Reactant 2

HCID 713Formamide

HCID 69803958HCID 69803958, compound

Product 1

HCID 9824224HCID 9824224, compoundYield 10.6%

Procedure

The procedure used for the preparation of Example 1, but replacing N-methylformamide with formamide, was used to prepare the title compound (0.059 g, 0.13 mmol, 10.6% yield) from 1-(3-bromoanilino) 4-[(2-methyl-4-pyridyl)methyl]phthalazine (for preparation see Novartis patent WO98/35958, 11.02.98). 1H-NMR (DMSO-d6) 9.31 (s, 1H), 8.58 (d, J=7.7, 1H), 8.49 (d, J=5.3, 1H), 8.35 (s, 1H), 8.13 (d, J=7.5, 1H), 8.05 (broad s, 1H), 7.89 to 7.99 (m, 4H), 7.59 (broad s, 1H), 7.53 (dd, J=5.1, 1.5, 1H), 7.29 (t, J=8.0, 1H), 7.18 (d, J=7.8, 1H), 4.68 (s, 2H); MS ES 434/436 (M+H)+ w/1Br, calc. 433; TLC (1:4:15 v/v methanol-acetone-dichloromethane) Rf=0.59.

Workup

customThe procedure used for the preparation of Example 1

Sources & evidence

ORD record: ord-40b64a3884b347cea1c60c1084103cf0
Source dataset: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06903101B1

Reaction notes

Loading…