Triethylamine → HCID 86618289, compound

HRID 2264582Notes

Reaction equation

HRID 2264582 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[F:13][C:14]([F:31])([F:30])[C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][C:21]=1[CH2:22][N:23]1[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]1)[NH2:18].CCN(CC)CC.[CH3:39][O:40][C:41]1[CH:51]=[CH:50][C:44]2[NH:45][CH2:46][CH2:47][CH2:48][CH2:49][C:43]=2[CH:42]=1>C(Cl)Cl.O.CCOC(C)=O>[F:31][C:14]([F:13])([F:30])[C:15]1[CH:16]=[C:17]([NH:18][C:2]([N:45]2[CH2:46][CH2:47][CH2:48][CH2:49][C:43]3[CH:42]=[C:41]([O:40][CH3:39])[CH:51]=[CH:50][C:44]2=3)=[O:4])[CH:19]=[CH:20][C:21]=1[CH2:22][N:23]1[CH2:24][CH2:25][N:26]([CH3:29])[CH2:27][CH2:28]1

Participants

8

Reactant 4

HCID 8471Triethylamine2×HCID 94429TriphosgeneHCID 122348407-Methoxy-2,3,4,5-tetrahydro-1H-benzo[b]azepine hydrochlorideHCID 46838908AP-24592

Product 1

HCID 86618289HCID 86618289, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

586 mg (1.97 mMol) triphosgene are dissolved in 70 ml ice-cooled CH2Cl2. Then a solution of 1618 mg (5.92 mMol) 3-trifluoromethyl-4-(4-methylpiperazin-1-ylmethyl)-aniline and 1.179 ml (8.46 mMol) Et3N in 12 ml CH2Cl2 is added during 11 min. After 3 additional minutes, the mixture is warmed up to rt by a water bath and then a solution of 1.00 g (5.64 mMol) of 7-methoxy-2,3,4,5-tetrahydro-1H-benzo[b]azepine [Monatsheft Chemie, 97 (1966), 150] and 786 μl (5.64 mMol) Et3N in 18 ml CH2Cl2 is added during 10 min. After 2 h at rt, the mixture is diluted with water and EtOAc, the aqueous phase separated off and extracted twice with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Column chromatography (SiO2; EtOAc/EtOH/NH3conc. 95:5:1→90:10:1) gives the title compound: MS: [M+1]+=477; HPLC: AtRet=12.0.

Workup

  1. customthe aqueous phase separated off
  2. extractionextracted twice with EtOAc
  3. washThe organic layers are washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fcfb836f124e4428af6a589b440e361b
Source dataset
uspto-grants-2010_12
Patent number
US07855215B2

Reaction notes

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