Triethylamine → HCID 89714664, compound

HRID 2273087Notes

Reaction equation

HRID 2273087 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[C:30]3[C:29](=[O:31])[N:28]([CH2:32][CH3:33])[CH2:27][C:26]([CH3:35])([CH3:34])[O:25][C:24]=3[N:23]=[C:22]([N:36]3[CH2:42][CH:41]4[O:43][CH:38]([CH2:39][CH2:40]4)[CH2:37]3)[N:21]=2)=[CH:16][C:15]=1[F:44].C(N(CC)CC)C.[NH2:52][C@H:53]([CH3:56])[CH2:54][OH:55]>C(Cl)Cl.O>[CH2:32]([N:28]1[CH2:27][C:26]([CH3:34])([CH3:35])[O:25][C:24]2[N:23]=[C:22]([N:36]3[CH2:37][CH:38]4[O:43][CH:41]([CH2:40][CH2:39]4)[CH2:42]3)[N:21]=[C:20]([C:17]3[CH:18]=[CH:19][C:14]([NH:13][C:2]([NH:52][C@H:53]([CH3:56])[CH2:54][OH:55])=[O:4])=[C:15]([F:44])[CH:16]=3)[C:30]=2[C:29]1=[O:31])[CH3:33]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 80308(R)-(-)-2-Amino-1-propanolHCID 94429TriphosgeneHCID 89714851HCID 89714851, compound

Product 1

HCID 89714664HCID 89714664, compoundYield 27.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 134.43 mg (0.45 mmol) of triphosgene, 200 mg (0.45 mmol) of 4-(4-amino-3-fluorophenyl)-6-ethyl-8,8-dimethyl-2-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-7,8-dihydro-6H-9-oxa-1,3,6-triazabenzocyclohepten-5-one and 275.04 mg (2.72 mmol) of triethylamine in 50 ml of DCM is stirred at room temperature for 30 minutes. 138.88 mg (1.81 mmol) of (R)-2-aminopropan-1-ol are then added and the mixture is stirred at room temperature for 2 hours. The resulting mixture is hydrolysed with 5 ml of water and the solvent is then evaporated off under reduced pressure. The product is precipitated by addition of ethyl acetate/water. The product is filtered off and solvents are evaporated off under reduced pressure to give 68 mg of 1-{4-[6-ethyl-8,8-dimethyl-2-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-5-oxo-5,6,7,8-tetrahydro-9-oxa-1,3,6-triazabenzocyclohepten-4-yl]-2-fluorophenyl}-3-((R)-2-hydroxy-1-methylethyl)urea.

Workup

  1. stirringthe mixture is stirred at room temperature for 2 hours
  2. customthe solvent is then evaporated off under reduced pressure
  3. customThe product is precipitated by addition of ethyl acetate/water
  4. filtrationThe product is filtered off
  5. customsolvents are evaporated off under reduced pressure

Sources & evidence

ORD record
ord-3ff969a4c0b94421af10a499dda07ecf
Source dataset
uspto-grants-2015_09
Patent number
US09120812B2

Reaction notes

Loading…