(R)-O-((2,2-Dimethyl-1,3-dioxolan-4-yl)methyl)hydroxylamine → 1-Cyclopropyl-3-(2-fluoro-4-iodo-phenylamino)-1-H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ((R)-2,3-dihydroxy-propoxy)-amide

HRID 2264982Notes

Reaction equation

HRID 2264982 reaction equation
[OH:1][CH:2]([CH2:29][OH:30])[CH2:3][O:4][NH:5][C:6]([C:8]1[N:16]([CH:17]2[CH2:19][CH2:18]2)[C:15]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[C:9]=1[NH:20][C:21]1[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=1[F:28])=[O:7].CC1(C)O[C@@H](CON)CO1>>[OH:1][C@H:2]([CH2:29][OH:30])[CH2:3][O:4][NH:5][C:6]([C:8]1[N:16]([CH:17]2[CH2:18][CH2:19]2)[C:15]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[C:9]=1[NH:20][C:21]1[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=1[F:28])=[O:7]

Participants

3

Reactant 2

HCID 11298047(R)-O-((2,2-Dimethyl-1,3-dioxolan-4-yl)methyl)hydroxylamineHCID 595966111-Cyclopropyl-3-(2-fluoro-4-iodo-phenylamino)-1H-pyrrolo[32-c]pyridine-2-carboxylic acid (2,3-dihydroxy-propoxy)-amide

Product 1

HCID 595965591-Cyclopropyl-3-(2-fluoro-4-iodo-phenylamino)-1-H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ((R)-2,3-dihydroxy-propoxy)-amide

Procedure

The title compound was prepared in an analogous fashion to 1-cyclopropyl-3-(2-fluoro-4-iodo-phenylamino)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid (2,3-dihydroxy-propoxy)-amide, replacing O-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-hydroxylamine with O—((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-hydroxylamine. 1H-NMR (500 MHz, DMSO-d6) δ ppm 11.60 (s, 1H), 8.53 (s, 1H), 8.32 (d, J=5.86 Hz, 1H), 7.57 (d, J=5.69 Hz, 1H), 7.53-7.48 (m, 2H), 7.20 (d, J=8.06 Hz, 1H), 6.26 (t, J=8.81 Hz, 1H), 4.87 (d, J=4.05 Hz, 1H), 4.60 (t, J=5.43 Hz, 1H), 3.94 (dd, J=9.88, 2.80 Hz, 1H), 3.76 (t, J=8.0 Hz, 1H), 3.70 (broad s, 1H), 3.56-3.45 (m, 1H), 3.40-3.34 (m, 2H), 1.15-1.08 (m, 2H), 0.88-0.83 (m, 2H); LC-MS (method E): [M+H]+=527.1, RT=7.31 min.

Sources & evidence

ORD record
ord-e5309b69ebdd4ae9945c8eb70c8b7ae5
Source dataset
uspto-grants-2010_12
Patent number
US07855216B2

Reaction notes

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