Triethylamine → tert-butyl 6-(2-amino-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidin-4-yl)octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate

HRID 1027884Notes

Reaction equation

HRID 1027884 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.[N:28]1([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:33][CH2:32][CH2:31][CH:30]2[CH2:34][NH:35][CH2:36][CH:29]12.C(N(CC)CC)C>C(#N)C>[NH2:18][C:16]1[N:17]=[C:12]([N:35]2[CH2:34][CH:30]3[CH:29]([N:28]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:33][CH2:32][CH2:31]3)[CH2:36]2)[C:13]2[CH2:23][CH2:22][CH2:21][C:20]3[CH:24]=[CH:25][CH:26]=[CH:27][C:19]=3[C:14]=2[N:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 225622021-Boc-octahydropyrrolo(3,4-b)pyridineHCID 251291732-amino-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidin-4-yl 4-methylbenzenesulfonate

Product 1

HCID 69224862tert-butyl 6-(2-amino-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-d]pyrimidin-4-yl)octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of the product from Example 59C (76 mg, 0.2 mmol), t-butyl octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate (CAS #159877-36-8) (59 mg, 0.22 mmol) and triethylamine (0.1 mL) in acetonitrile (1 mL) was heated in a microwave reactor at 160° C. for 1 hour. The mixture was concentrated and chromatographed on silica gel eluting with EtOAc:hexane (1:1) mixture to yield the title compound.

Workup

  1. concentrationThe mixture was concentrated
  2. customchromatographed on silica gel eluting with EtOAc:hexane (1:1) mixture

Sources & evidence

ORD record
ord-ed8e397379d34cf5a26240da5af9ba5a
Source dataset
uspto-grants-2014_05
Patent number
US08735411B2

Reaction notes

Loading…