HCID 24808467, compound → [3-(2-Fluoro-4-iodo-phenylamino)-1H-pyrrolo[3,2-c]pyridin-2-yl]-((2S,4R)-4-hydroxy-2-hydroxymethyl-pyrrolidin-1-yl)-methanone

HRID 2264984Notes

Reaction equation

HRID 2264984 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:14]2[CH:15]=[N:16][CH:17]=[CH:18][C:13]=2[NH:12][C:11]=1[C:19]([N:21]1[CH2:25][CH2:24][C@@H:23]([OH:26])[CH2:22]1)=[O:20].Cl.[OH:28][CH2:29][C@H]1NC[C@H](O)C1>>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:14]2[CH:15]=[N:16][CH:17]=[CH:18][C:13]=2[NH:12][C:11]=1[C:19]([N:21]1[CH2:22][C@H:23]([OH:26])[CH2:24][C@H:25]1[CH2:29][OH:28])=[O:20]

Participants

3

Reactant 2

HCID 24808467HCID 24808467, compoundHCID 53487134(3R,5S)-5-(hydroxymethyl)pyrrolidin-3-ol hydrochloride

Product 1

HCID 59596462[3-(2-Fluoro-4-iodo-phenylamino)-1H-pyrrolo[3,2-c]pyridin-2-yl]-((2S,4R)-4-hydroxy-2-hydroxymethyl-pyrrolidin-1-yl)-methanone

Procedure

The title compound was prepared in an analogous fashion to [3-(2-fluoro-4-iodo-phenylamino)-1H-pyrrolo[3,2-c]pyridin-2-yl]-((R)-3-hydroxy-pyrrolidin-1-yl)-methanone, replacing (R)-pyrrolidin-3-ol hydrochloride with (3R,5S)-5-hydroxymethyl-pyrrolidin-3-ol hydrochloride. 1H-NMR (400 MHz, MeOD) 6 ppm 8.62 (d, J=1.02 Hz, 1H), 8.23 (d, J=5.99 Hz, 1H), 7.52-7.35 (m, 2H), 7.34-7.16 (m, 1H), 6.60 (t, J=8.8 Hz, 1H), 4.59-4.42 (m, 1H), 4.35-4.17 (m, 1H), 3.71-3.44 (m, 4H), 2.19-1.90 (m, 2H); LC-MS (method E): [M+H]+=497.1, RT=3.37 min.

Sources & evidence

ORD record
ord-cb6d56c6ec264d8f907cbdc86e19a021
Source dataset
uspto-grants-2010_12
Patent number
US07855216B2

Reaction notes

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