O-(cyclopropylmethyl)hydroxylamine hydrochloride → N-(cyclopropylmethoxy)-5-(2-fluoro-4-iodophenylamino)imidazo[1,5-a]pyrazine-6-carboxamide

HRID 1500734Notes

Reaction equation

HRID 1500734 reaction equation
[CH2:1]([O:3][NH:4][C:5]([C:7]1[N:8]=[CH:9][C:10]2[N:11]([CH:22]=[N:23][CH:24]=2)[C:12]=1[NH:13][C:14]1[CH:19]=[CH:18][C:17]([I:20])=[CH:16][C:15]=1[F:21])=[O:6])[CH3:2].Cl.[CH:26]1(CON)C[CH2:27]1>>[CH:2]1([CH2:1][O:3][NH:4][C:5]([C:7]2[N:8]=[CH:9][C:10]3[N:11]([CH:22]=[N:23][CH:24]=3)[C:12]=2[NH:13][C:14]2[CH:19]=[CH:18][C:17]([I:20])=[CH:16][C:15]=2[F:21])=[O:6])[CH2:27][CH2:26]1

Participants

3

Reactant 2

HCID 11557279O-(cyclopropylmethyl)hydroxylamine hydrochlorideHCID 44135982HCID 44135982, compound

Product 1

HCID 44135983N-(cyclopropylmethoxy)-5-(2-fluoro-4-iodophenylamino)imidazo[1,5-a]pyrazine-6-carboxamide

Procedure

The title compound was prepared in an analogous fashion to N-ethoxy-5-(2-fluoro-4-iodophenylamino)imidazo[1,5-a]pyrazine-6-carboxamide, using O-(cyclopropylmethyl)-hydroxylamine hydrochloride as the starting material. 1H NMR (DMSO-d6, 400 MHz) δ ppm 11.82 (s, 1H), 10.36 (s, 1H), 8.82 (s, 1H), 7.95 (s, 1H), 7.91 (s, 1H), 7.73 (dd, J=10.4 Hz, 1.8 Hz, 1H), 7.44 (d, 8.4 Hz, 1H), 6.58 (t, J=8.4 Hz, 1H), 3.67 (d, J=7.2 Hz, 2H), 1.12 to 1.01 (m, 1H), 0.54-0.48 (m, 2H), 0.28-0.23 (m, 2H); LCMS (method D2): RT=1.33 min, [M+H]+=468.

Sources & evidence

ORD record
ord-3f582e7d915242f9a9e3cfdc191eb996
Source dataset
uspto-grants-2015_12
Patent number
US09206174B2

Reaction notes

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