Trifluoroacetic acid → 4-Octahydro-6h-pyrrolo[3,4-b]pyridin-6-yl-6,7-dihydro-5h-benzo[6,7]cyclohepta[1,2-d]pyrimidin-2-amine

HRID 1027885Notes

Reaction equation

HRID 1027885 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([N:17]2[CH2:25][CH:24]3[CH:19]([N:20](C(OC(C)(C)C)=O)[CH2:21][CH2:22][CH2:23]3)[CH2:18]2)[C:5]2[CH2:12][CH2:11][CH2:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[C:6]=2[N:7]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH:20]1[CH2:21][CH2:22][CH2:23][CH:24]2[CH2:25][N:17]([C:4]3[C:5]4[CH2:12][CH2:11][CH2:10][C:9]5[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=5[C:6]=4[N:7]=[C:2]([NH2:1])[N:3]=3)[CH2:18][CH:19]12

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 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

Product 1

HCID 597743544-Octahydro-6h-pyrrolo[3,4-b]pyridin-6-yl-6,7-dihydro-5h-benzo[6,7]cyclohepta[1,2-d]pyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 59D in CH2Cl2 (2 mL) was treated with trifluoroacetic acid (0.5 mL), stirred for 2 hours, concentrated and partitioned between 1M NaOH solution and CH2Cl2. The organic layer was isolated, dried over MgSO4 and concentrated to yield the title product. 1H NMR (CDCl3) δ 0.86 (m, 1H), 1.77 (m, 5H), 2.16 (m, 2H), 2.30 (m, 1H), 2.64 (m, 3H), 3.03 (m, 1H), 3.43 (m, 3H), 3.87 (m, 2H), 4.73 (bs, 2H), 7.19 (m, 1H), 7.33, (m, 2H), 7.75 (m, 1H). MS (M+H)+ m/z 336.

Workup

  1. concentrationconcentrated
  2. custompartitioned between 1M NaOH solution and CH2Cl2
  3. customThe organic layer was isolated
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5cdc290f9d9b408e93dcd486e11ffa7f
Source dataset
uspto-grants-2014_05
Patent number
US08735411B2

Reaction notes

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