Triethylamine → HCID 89714813, compound

HRID 2273078Notes

Reaction equation

HRID 2273078 reaction equation
ClC(Cl)(O[C:5](=[O:11])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][CH:15]=1.C(N(CC)CC)C.[F:51][C:52]1[CH:58]=[C:57]([F:59])[CH:56]=[CH:55][C:53]=1[NH2:54]>C(Cl)Cl>[F:51][C:52]1[CH:58]=[C:57]([F:59])[CH:56]=[CH:55][C:53]=1[NH:54][C:5]([NH:13][C:14]1[CH:15]=[CH:16][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[CH2:37][CH:38]4[O:43][CH:41]([CH2:40][CH2:39]4)[CH2:42]3)[N:21]=2)=[CH:18][CH:19]=1)=[O:11]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 97092,4-DifluoroanilineHCID 94429TriphosgeneHCID 89714581HCID 89714581, compound

Product 1

HCID 89714813HCID 89714813, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 350.35 mg (1.18 mmol) of triphosgene in 6 ml of DCM is added in a single portion a suspension of 500 mg (1.18 mmol) of 4-(4-aminophenyl)-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 987.33 μl (7.08 mmol) of triethylamine in 6 ml of DCM. The resulting mixture is stirred for 20 minutes at room temperature. 607.12 μl (5.90 mmol) of 2,4-difluoroaniline are added. The precipitate obtained is filtered off, rinsed twice with MeOH and dried under reduced pressure to give 575 mg of 1-(2,4-difluorophenyl)-3-{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]phenyl}urea.

Workup

  1. customThe precipitate obtained
  2. filtrationis filtered off
  3. washrinsed twice with MeOH
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-509da162a0cf4e16959b9339635aea3a
Source dataset
uspto-grants-2015_09
Patent number
US09120812B2

Reaction notes

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