1-Boc-3-aminopyrrolidine → HCID 56848567, compound

HRID 1470345Notes

Reaction equation

HRID 1470345 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[O:21][C:20]3[C:15](=[N:16][CH:17]=[CH:18][C:19]=3[C:22]3[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=3)[C:25](O)=[O:26])[CH:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[NH2:31][CH:32]1[CH2:36][CH2:35][N:34]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:33]1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[O:21][C:20]3[C:15](=[N:16][CH:17]=[CH:18][C:19]=3[C:22]3[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=3)[C:25]([NH:31][CH:32]3[CH2:36][CH2:35][N:34]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:33]3)=[O:26])[CH:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]

Participants

3

Reactant 2

HCID 27563701-Boc-3-aminopyrrolidineHCID 66779501HCID 66779501, compound

Product 1

HCID 56848567HCID 56848567, compoundYield 64%

Procedure

Starting from 3-[2-(3,4,5-trimethoxyphenyl)furo[3,2-b]pyridin-7-yl]benzoic acid (0.099 mmol) and (+/−)-3-amino-1-N—BOC-pyrrolidine (0.102 mmol) the product is prepared analogously to “A43” and obtained as yellow solid in a yield of 64%. HPLC (method A): Rt 2.68 min (purity 99.3%); LCMS (ESI+) (method E): Rt 2.11 min, M+H+ 574.3 m/z; 1H NMR (500 MHz, DMSO-d6) δ[ppm] 8.82 (s, 1H), 8.71 (d, J=6.3, 1H), 8.62 (d, J=5.2, 1H), 8.28 (d, J=8.0, 1H), 8.06 (d, J=7.9, 1H), 7.79 (s, 1H), 7.74 (dd, J=13.0, 6.4, 2H), 7.37 (s, 2H), 4.46 (s, 1H), 3.93 (s, 6H), 3.75 (s, 3H), 3.48-3.39 (m, 1H), 3.34 (d, J=7.0, 2H), 3.22 (d, J=4.2, 1H), 2.19-2.09 (m, 1H), 1.99-1.86 (m, 1H), 1.41 (s, 9H).

Workup

  1. customis prepared analogously to “A43”
  2. customobtained as yellow solid in a yield of 64%

Sources & evidence

ORD record
ord-8794dbe119094d798c43f76abffd9a5c
Source dataset
uspto-grants-2015_04
Patent number
US09006440B2

Reaction notes

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