3-Chloro-4-fluoroaniline → HCID 69794445, compound

HRID 1072144Notes

Reaction equation

HRID 1072144 reaction equation
Cl[C:2]1[C:3]2[C:10](=[CH:11][C:12]3[NH:13][C:14]([CH3:18])=[CH:15][C:16]=3[CH3:17])[C:9](=[O:19])[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[Cl:20][C:21]1[CH:22]=[C:23]([NH2:28])[CH:24]=[CH:25][C:26]=1[F:27]>>[Cl:20][C:21]1[CH:22]=[C:23]([NH:28][C:2]2[C:3]3[C:10](=[CH:11][C:12]4[NH:13][C:14]([CH3:18])=[CH:15][C:16]=4[CH3:17])[C:9](=[O:19])[NH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH:24]=[CH:25][C:26]=1[F:27]

Participants

3

Reactant 2

HCID 97083-Chloro-4-fluoroanilineHCID 73885145HCID 73885145, compound2×

Product 1

HCID 69794445HCID 69794445, compoundYield 57%

Procedure

The title compound (57% yield) was prepared from 4-chloro-5-(3,5-dimethyl-1H-pyrrol-2-ylmethylene)-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one and 3-chloro-4-fluoro-phenylamine according to the procedure described for Example 12 without the conversion to the HCl salt. 1H NMR (360 MHz, DMSO-d6) δ 13.10 (br s, 1H, NH), 11.60 (br s, 1H, NH), 9.10 (s, 1H), 8.27 (s, 1H, H-vinyl), 7.70 (m, 1H), 7.3-7.4 (m, 3H), 6.04 (br s, 1H), 2.33 (s, 3H, CH3), 2.16 (s, 3H, CH3). MS 384.3 [M++1].

Sources & evidence

ORD record
ord-0f543f21f24f4e0a9aaf59469eee05c5
Source dataset
uspto-grants-2005_06
Patent number
US06908930B2

Reaction notes

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