Trifluoroacetic acid methylene chloride → 6-(2,7-Diaza-spiro[3.5]non-7-ylmethyl)-2-(6-fluoro-1H-indol-4-yl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine

HRID 2066557Notes

Reaction equation

HRID 2066557 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[C:4]([C:11]2[N:12]=[C:13]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)[C:14]3[S:19][C:18]([CH2:20][N:21]4[CH2:26][CH2:25]N5C[CH2:28][CH2:29][C@H:23]5[CH2:22]4)=[CH:17][C:15]=3[N:16]=2)[CH:3]=1.Cl.C(O[C:42]([N:44]1CC2(CCNCC2)C1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)Cl>>[CH2:42]1[C:29]2([CH2:23][CH2:22][N:21]([CH2:20][C:18]3[S:19][C:14]4[C:13]([N:30]5[CH2:35][CH2:34][O:33][CH2:32][CH2:31]5)=[N:12][C:11]([C:4]5[CH:3]=[C:2]([F:1])[CH:10]=[C:9]6[C:5]=5[CH:6]=[CH:7][NH:8]6)=[N:16][C:15]=4[CH:17]=3)[CH2:26][CH2:25]2)[CH2:28][NH:44]1

Participants

4

Reactant 3

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 24820549tert-Butyl 2,7-diazaspiro[3.5]nonane-2-carboxylate hydrochlorideHCID 581170432-(6-fluoro-1H-indol-4-yl)-6-[(5)-1-(hexahydro-pyrrolo[1,2-a]pyrazin-2-yl)methyl]-4-morpholin-4-yl-thieno-[3,2-d]pyrimidine

Product 1

HCID 462399976-(2,7-Diaza-spiro[3.5]non-7-ylmethyl)-2-(6-fluoro-1H-indol-4-yl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine

Procedure

Prepared according to the method used in the preparation of 2-(6-fluoro-1H-indol-4-yl)-6-[(S)-1-(hexahydro-pyrrolo[1,2-a]pyrazin-2-yl)methyl]-4-morpholin-4-yl-thieno-[3,2-d]pyrimidine using 2,7-diaza-spiro[3.5]nonane-2-carboxylic acid tert-butyl ester hydrochloride in place of (S)-octahydro-pyrrolo[1,2-a]pyrazine, followed by BOC-deprotection using TFA:DCM (1:1). The title compound was obtained as a white solid (27 mg, 44%).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-fcebd5b7af4a4e4cb3b95177bc0b20a6
Source dataset
uspto-grants-2012_10
Patent number
US08293735B2

Reaction notes

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