Triethylamine → HCID 67459937, compound

HRID 625051Notes

Reaction equation

HRID 625051 reaction equation
[N:1]1([C:7]2[C:8]3[CH2:15][S:14][CH2:13][C:9]=3[N:10]=[CH:11][N:12]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:23]([O:27][C:28]([NH:30][C@H:31]([CH2:35][C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=1)[C:32](O)=[O:33])=[O:29])([CH3:26])([CH3:25])[CH3:24].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[Cl:42][C:39]1[CH:40]=[CH:41][C:36]([CH2:35][C@@H:31]([NH:30][C:28](=[O:29])[O:27][C:23]([CH3:25])([CH3:24])[CH3:26])[C:32]([N:4]2[CH2:5][CH2:6][N:1]([C:7]3[C:8]4[CH2:15][S:14][CH2:13][C:9]=4[N:10]=[CH:11][N:12]=3)[CH2:2][CH2:3]2)=[O:33])=[CH:37][CH:38]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 7018791N-Boc-4-chloro-D-phenylalanineHCID 67459054HCID 67459054, compound

Product 1

HCID 67459937HCID 67459937, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(piperazin-1-yl)-5,7-dihydrothieno[3,4-d]pyrimidine (0.28 g, 1.3 mmol) in CH2Cl2 (20 mL) was added triethylamine (5 mL) and (R)-2-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)propanoic acid (0.38 g, 1.3 mmol). After stirring for 30 minutes, HBTU (0.57 g, 1.5 mmol) was added. The mix was stirred at room temperature for 1 hour. The solvent was removed and the residue was subject to silica gel chromatography, eluting with hexane/ethyl acetate (1:1) to give (R)-tert-butyl 3-(4-chlorophenyl)-1-(4-(5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazin-1-yl)-1-oxopropan-2-ylcarbamate (0.62 g, 98%). 1H NMR (CDCl3, 400 MHz) δ 8.49 (s, 1H), 5.38-5.35 (m, 1H), 3.70-3.50 (m, 6H), 3.27-3.13 (m, 2H), 2.98-2.92 (m, 2H), 1.42 (s, 9H). MS (APCI+) [M+H]+ 505.

Workup

  1. stirringThe mix was stirred at room temperature for 1 hour
  2. customThe solvent was removed
  3. washeluting with hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-a12800eccf5648bf827a876d1e5dd27a
Source dataset
uspto-grants-2016_04
Patent number
US09303040B2

Reaction notes

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