Triethylamine → HCID 57848474, compound

HRID 2267271Notes

Reaction equation

HRID 2267271 reaction equation
[O:1]=[C:2]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C@@H:18]([C:32](O)=[O:33])[CH2:19][C:20]3[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[C:23]([NH2:30])=[C:22]([Cl:31])[CH:21]=3)=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:35]=[CH:36][CH:37]=[CH:38][C:4]=2[NH:3]1.[N:39]1([CH:45]2[CH2:50][CH2:49][N:48](C(OCC3C=CC=CC=3)=O)[CH2:47][CH2:46]2)[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[O:1]=[C:2]1[N:8]([CH:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C@H:18]([CH2:19][C:20]3[CH:25]=[C:24]([C:26]([F:29])([F:27])[F:28])[C:23]([NH2:30])=[C:22]([Cl:31])[CH:21]=3)[C:32](=[O:33])[N:42]3[CH2:41][CH2:40][N:39]([CH:45]4[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]4)[CH2:44][CH2:43]3)=[O:16])[CH2:13][CH2:14]2)[CH2:7][CH2:6][C:5]2[CH:35]=[CH:36][CH:37]=[CH:38][C:4]=2[NH:3]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 57807329HCID 57807329, compoundHCID 58202073(R)-2-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-1-carboxy-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

Product 1

HCID 57848474HCID 57848474, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.00 g (1.80 mmol) (R)-2-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-1-carboxy-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate (Example 1f), 546 mg (1.80 mmol) benzyl 4-piperazin-1-yl -piperidine-1-carboxylate (Example A17b), 643 mg (2.00 mmol) TBTU and 0.35 mL (2.50 mmol) triethylamine in 10 mL DMF was stirred overnight at RT. This was combined with 150 mL of 15% K2CO3 solution, the precipitate was removed by suction filtering, washed with 30 mL water and the crude product was dried at 40° C. in the drying cupboard.

Workup

  1. customthe precipitate was removed by suction
  2. filtrationfiltering
  3. washwashed with 30 mL water
  4. dry with materialthe crude product was dried at 40° C. in the drying cupboard

Sources & evidence

ORD record
ord-47470b95ad8f4eaba43eff61ae2df936
Source dataset
uspto-grants-2010_12
Patent number
US07858622B2

Reaction notes

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