Triethylamine → HCID 10327519, compound

HRID 736926Notes

Reaction equation

HRID 736926 reaction equation
[NH2:1][C:2]1[C:28]([C:29]([F:32])([F:31])[F:30])=[CH:27][C:5]([CH2:6][C@H:7]([C:12]([N:14]2[CH2:19][CH2:18][CH:17]([N:20]3[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]3)[CH2:16][CH2:15]2)=[O:13])[CH2:8][C:9]([OH:11])=O)=[CH:4][C:3]=1[Cl:33].[NH:34]1[CH2:39][CH2:38][CH:37]([N:40]2[CH2:46][CH2:45][C:44]3[CH:47]=[CH:48][CH:49]=[CH:50][C:43]=3[NH:42][C:41]2=[O:51])[CH2:36][CH2:35]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C=O)C>[NH2:1][C:2]1[C:28]([C:29]([F:30])([F:31])[F:32])=[CH:27][C:5]([CH2:6][C@@H:7]([CH2:8][C:9]([N:34]2[CH2:35][CH2:36][CH:37]([N:40]3[CH2:46][CH2:45][C:44]4[CH:47]=[CH:48][CH:49]=[CH:50][C:43]=4[NH:42][C:41]3=[O:51])[CH2:38][CH2:39]2)=[O:11])[C:12]([N:14]2[CH2:15][CH2:16][CH:17]([N:20]3[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]3)[CH2:18][CH2:19]2)=[O:13])=[CH:4][C:3]=1[Cl:33]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 113795873-(Piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-oneHCID 12094439HCID 12094439, compound

Product 1

HCID 10327519HCID 10327519, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6.3 g (12.8 mmol) of (S)-3-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-4-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-4-oxo-butanoic acid, 3.16 g (12.9 mmol) of 3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one, 4.66 g (14.5 mmol) of TBTU, 1.96 g (14.5 mmol) of HOBt, 9.45 mL (68 mmol) of triethylamine and 300 mL DMF was stirred for 12 h at RT. The reaction mixture was evaporated down i. vac., the residue was distributed between EtOAc and saturated NaHCO3 solution. The org. phase was separated off, dried and evaporated down i. vac. The residue was purified by chromatography on silica gel. The yellow oil obtained was triturated with ether and suction filtered. The desired product was obtained in the form of a white solid.

Workup

  1. customThe reaction mixture was evaporated down i
  2. customphase was separated off
  3. customdried
  4. customevaporated down i
  5. customThe residue was purified by chromatography on silica gel
  6. customThe yellow oil obtained
  7. customwas triturated with ether and suction
  8. filtrationfiltered

Sources & evidence

ORD record
ord-d67b8e480cfe4a5ea13f72d3334cbe8f
Source dataset
uspto-grants-2009_09
Patent number
US07595312B2

Reaction notes

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