Triethylamine → HCID 68761423, compound

HRID 529134Notes

Reaction equation

HRID 529134 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]2[N:9]([C:24]3[C:25]4[C@H:32]([CH3:33])[CH2:31][CH2:30][C:26]=4[N:27]=[CH:28][N:29]=3)[CH2:10][C:11]3([CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)[C:4]=12.Cl[C:35]1[N:40]=[CH:39][CH:38]=[CH:37][N:36]=1.C(N(CC)CC)C>CN(C=O)C.CO>[CH3:33][C@H:32]1[C:25]2[C:24]([N:9]3[C:5]4[C:4](=[C:3]([CH2:2][NH:1][C:35]5[N:40]=[CH:39][CH:38]=[CH:37][N:36]=5)[CH:8]=[CH:7][CH:6]=4)[C:11]4([CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[CH2:13][CH2:12]4)[CH2:10]3)=[N:29][CH:28]=[N:27][C:26]=2[CH2:30][CH2:31]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 744042-ChloropyrimidineHCID 69810509HCID 69810509, compound

Product 1

HCID 68761423HCID 68761423, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of (R)-tert-butyl 4-(aminomethyl)-1-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-1′-carboxylate (15 mg, 0.033 mmol), 2-chloropyrimidine (3.8 mg, 0.033 mmol), and triethylamine (25 μL, 0.16 mmol) in DMF (0.50 mL) was heated at 100° C. for 24 hours. The material was diluted with MeOH and purified with a Gilson C18 prep HPLC system to give (R)-tert-butyl 1-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)-4-((pyrimidin-2-ylamino)methyl)spiro[indoline-3,4′-piperidine]-1′-carboxylate (7.0 mg, 0.013 mmol, 40%). LCMS (APCI+) M+H+ 528 (85%); Rt=3.89 min.

Workup

  1. custompurified with a Gilson C18 prep HPLC system

Sources & evidence

ORD record
ord-c214a1040228477d8999271ffbaec29d
Source dataset
uspto-grants-2016_05
Patent number
US09346805B2

Reaction notes

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