Triethylamine → 5-(6-(3,3-dimethylpiperidine-1-carbonyl)pyrimidin-4-ylamino)-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

HRID 1640270Notes

Reaction equation

HRID 1640270 reaction equation
Cl.[O:2]=[C:3]1[NH:11][C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[C:4]21[CH2:19][C:18]1[C:13](=[CH:14][CH:15]=[C:16]([NH:20][C:21]3[N:26]=[CH:25][N:24]=[C:23]([C:27]([OH:29])=O)[CH:22]=3)[CH:17]=1)[CH2:12]2.[CH3:30][C:31]1([CH3:37])[CH2:36][CH2:35][CH2:34][NH:33][CH2:32]1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[CH3:30][C:31]1([CH3:37])[CH2:36][CH2:35][CH2:34][N:33]([C:27]([C:23]2[N:24]=[CH:25][N:26]=[C:21]([NH:20][C:16]3[CH:17]=[C:18]4[C:13](=[CH:14][CH:15]=3)[CH2:12][C:4]3([C:5]5[C:6](=[N:7][CH:8]=[CH:9][CH:10]=5)[NH:11][C:3]3=[O:2])[CH2:19]4)[CH:22]=2)=[O:29])[CH2:32]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 709423,3-DimethylpiperidineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 667221856-(2'-Oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-yl-amino)pyrimidine-4-carboxylic acid-hydrochloride

Product 1

HCID 498005155-(6-(3,3-dimethylpiperidine-1-carbonyl)pyrimidin-4-ylamino)-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

82 mg (0.20 mmol) 6-(2′-oxo-1,1′,2′,3-tetrahydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-5-ylamino)pyrimidine-4-carboxylic acid hydrochloride, 32 mg (0.27 mmol) 3,3-dimethyl-piperidine, 80 μL (0.57 mmol) triethylamine and 70 mg (0.22 mmol) TBTU in 0.80 mL DMF were stirred overnight at RT. The purification was carried out by preparative HPLC-MS. The product-containing fractions were combined and lyophilised.

Workup

  1. customThe purification

Sources & evidence

ORD record
ord-d22f492f02504a8983f81e4afccde684
Source dataset
uspto-grants-2012_02
Patent number
US08110575B2

Reaction notes

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