9-(1-Isopropyl-piperidin-4-yloxy)-2,3,4,5-tetrahydro-[1,4]diazepino[1,2-a]indol-1-one → 5-Benzyloxy-1-(2-tert-butoxycarbonylamino-ethyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid methyl ester

HRID 506743Notes

Reaction equation

HRID 506743 reaction equation
C(N1CCC(OC2C=CC3N4CCCNC(=O)C4=CC=3C=2)CC1)(C)C.[CH3:26][O:27][C:28]([C:30]1[N:46](C(OC(C)(C)C)=O)[C:33]2=[N:34][CH:35]=[C:36]([O:38][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[CH:37]=[C:32]2[CH:31]=1)=[O:29].[C:54]([O:58][C:59]([N:61]1[CH2:65][CH2:64]OS1(=O)=O)=[O:60])([CH3:57])([CH3:56])[CH3:55].CC(C)([O-])C.[K+]>>[CH3:26][O:27][C:28]([C:30]1[N:46]([CH2:64][CH2:65][NH:61][C:59]([O:58][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:60])[C:33]2=[N:34][CH:35]=[C:36]([O:38][CH2:39][C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH:37]=[C:32]2[CH:31]=1)=[O:29]

Participants

5

Reactant 4

HCID 166797019-(1-Isopropyl-piperidin-4-yloxy)-2,3,4,5-tetrahydro-[1,4]diazepino[1,2-a]indol-1-oneHCID 235840203-Boc-1,2,3-oxathiazolidine 2,2-dioxideHCID 23665647Potassium tert-butoxideHCID 684233055-Benzyloxy-pyrrolo[2,3-b]pyridine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester2×

Product 1

HCID 684633515-Benzyloxy-1-(2-tert-butoxycarbonylamino-ethyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid methyl ester

Procedure

The title compound was synthesized in analogy to example 1, intermediate b), from 5-benzyloxy-pyrrolo[2,3-b]pyridine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (intermediate M), 2,2-dioxo-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester (prepared according to WO02/072584) and potassium tert-butoxide, to give the product as a colorless foam (89%).

Sources & evidence

ORD record
ord-3c467e8463d44f4399ddf5b13177d774
Source dataset
uspto-grants-2010_08
Patent number
US07786109B2

Reaction notes

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