tert-Butyl spiro(indole-3,4'-piperidine)-1(2H)-carboxylate → 7-Benzylamino-6-(1-(tert-butoxycarbonyl)spiro[indoline-3,4'-piperidine]-1'-ylcarbonyl)-3-ethoxycarbonylpyrazolo[1,5-a]pyrimidine

HRID 1027127Notes

Reaction equation

HRID 1027127 reaction equation
[CH2:1]([NH:8][C:9]1[N:14]2[N:15]=[CH:16][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:13]2[N:12]=[CH:11][C:10]=1[C:23](O)=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:26]1[CH2:31][CH2:30][C:29]2([C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[N:33]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:32]2)[CH2:28][CH2:27]1>>[CH2:1]([NH:8][C:9]1[N:14]2[N:15]=[CH:16][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:13]2[N:12]=[CH:11][C:10]=1[C:23]([N:26]1[CH2:27][CH2:28][C:29]2([C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[N:33]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:32]2)[CH2:30][CH2:31]1)=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 23572861tert-Butyl spiro(indole-3,4'-piperidine)-1(2H)-carboxylateHCID 675407947-Benzylamino-3-ethoxycarbonylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid

Product 1

HCID 675408247-Benzylamino-6-(1-(tert-butoxycarbonyl)spiro[indoline-3,4'-piperidine]-1'-ylcarbonyl)-3-ethoxycarbonylpyrazolo[1,5-a]pyrimidineYield 79.3%

Procedure

In the same manner as in Example 21, step 5 and using 7-benzylamino-3-ethoxycarbonylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid (0.363 g, 1.07 mmol) obtained in Example 21, step 4 and tert-butyl spiro[indoline-3,4′-piperidine]-1-carboxylate (0.370 g, 1.28 mmmol) obtained in Reference Example 8, the title compound (0.518 g, 79%) was obtained.

Workup

  1. customobtained in Reference Example 8

Sources & evidence

ORD record
ord-0391bfd0e71f41e083001f258de22ecd
Source dataset
uspto-grants-2014_05
Patent number
US08729264B2

Reaction notes

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