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Triethylamine → 4-((3R)-3-(t-Butoxycarbonyl)Amino-pyrrolidin-1-yl)-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidin-2-ylamine

HRID 1014933
Notes
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Reaction equation

HRID 1014933 reaction equation
CC1C=CC(S(O[C:12]2[C:13]3[CH2:23][CH2:22][CH2:21][C:20]4[CH:24]=[CH:25][CH:26]=[CH:27][C:19]=4[C:14]=3[N:15]=[C:16]([NH2:18])[N:17]=2)(=O)=O)=CC=1.[NH:28]1[CH2:32][CH2:31][C@@H:30]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[CH2:29]1.C(N(CC)CC)C>C(#N)C.CCOC(C)=O>[C:36]([O:35][C:34]([NH:33][C@@H:30]1[CH2:31][CH2:32][N:28]([C:12]2[C:13]3[CH2:23][CH2:22][CH2:21][C:20]4[CH:24]=[CH:25][CH:26]=[CH:27][C:19]=4[C:14]=3[N:15]=[C:16]([NH2:18])[N:17]=2)[CH2:29]1)=[O:40])([CH3:39])([CH3:37])[CH3:38]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 251291732-amino-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidin-4-yl 4-methylbenzenesulfonate

Product 1

HCID 597768164-((3R)-3-(t-Butoxycarbonyl)Amino-pyrrolidin-1-yl)-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidin-2-ylamine

Reagents, catalysts & solvents 2

HCID 6342
Acetonitrile
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

A solution of the product from Example 4C (1.5 g, 3.93 mmol), (R)-tert-butyl pyrrolidin-3-ylcarbamate (CAS #: 122536-77-0) (1.1 g, 5.9 mmol) and triethylamine (0.9 mL, 5.9 mmol) in acetonitrile (35 mL) was heated to 80° C. for 16 hours. The mixture was cooled to room temperature, diluted with EtOAc, washed with H2O and brine, dried (MgSO4), concentrated and chromatographed on silica gel eluting with ethyl acetate to provide the title compound.

Workup

  1. washwashed with H2O and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customchromatographed on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-aa7f8394e9a048cc93f5c92b9e9d2583
Source dataset
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07985745B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes