N-(cyclopropylmethoxy)-5-(2-fluoro-4-iodophenylamino)imidazo[1,5-a]pyrazine-6-carboxamide → 5-(4-Bromo-2-fluorophenylamino)-N-(cyclopropyl-methoxy)imidazo[1,5-a]pyrazine-6-carboxamide

HRID 2076227Notes

Reaction equation

HRID 2076227 reaction equation
[CH:1]1([CH2:4][O:5][NH:6][C:7]([C:9]2[N:10]=[CH:11][C:12]3[N:13]([CH:24]=[N:25][CH:26]=3)[C:14]=2[NH:15][C:16]2[CH:21]=[CH:20][C:19](I)=[CH:18][C:17]=2[F:23])=[O:8])[CH2:3][CH2:2]1.COC(C1N=CC2N(C=NC=2)C=1NC1C=CC([Br:44])=CC=1F)=O>>[Br:44][C:19]1[CH:20]=[CH:21][C:16]([NH:15][C:14]2[N:13]3[CH:24]=[N:25][CH:26]=[C:12]3[CH:11]=[N:10][C:9]=2[C:7]([NH:6][O:5][CH2:4][CH:1]2[CH2:3][CH2:2]2)=[O:8])=[C:17]([F:23])[CH:18]=1

Participants

3

Reactant 2

HCID 44135983N-(cyclopropylmethoxy)-5-(2-fluoro-4-iodophenylamino)imidazo[1,5-a]pyrazine-6-carboxamideHCID 591401755-(4-Bromo-2-fluoro-phenylamino)-imidazo[1,5-a]pyrazine-6-carboxylic acid methyl ester

Product 1

HCID 441361065-(4-Bromo-2-fluorophenylamino)-N-(cyclopropyl-methoxy)imidazo[1,5-a]pyrazine-6-carboxamide

Procedure

The title compound was prepared in an analogous fashion to N-(cyclopropylmethoxy)-5-(2-fluoro-4-iodophenylamino)imidazo[1,5-a]pyrazine-6-carboxamide, using 5-(4-bromo-2-fluoro-phenylamino)-imidazo[1,5-a]pyrazine-6-carboxylic acid methyl ester as the starting material. 1H NMR (MeOD, 400 MHz) δ ppm 8.74 (s, 1H), 7.87 (s, 1H), 7.84 (s, 1H), 7.48 (dd, J=10.4 Hz, 3.2 Hz, 1H), 7.30 (d, 8.4 Hz, 1H), 6.75 (t, J=8.4 Hz, 1H), 3.79 (d, J=7.2 Hz, 2H), 1.26-1.13 (m, 1H), 0.62-0.55 (m, 2H), 0.36 to 0.30 (m, 2H); LCMS (method D1): RT=0.985 min, [M+H]+=420/422.

Sources & evidence

ORD record
ord-545963fb6d1a4b028dc0c28b3b65beaa
Source dataset
uspto-grants-2011_04
Patent number
US07923456B2

Reaction notes

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