Dichloromethane → HCID 14835257, compound

HRID 1089301Notes

Reaction equation

HRID 1089301 reaction equation
C(Cl)Cl.[OH:4][C@H:5]1[C@@H:11]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH2:10][C:9]2[C:20]([C:24]([F:27])([F:26])[F:25])=[CH:21][CH:22]=[CH:23][C:8]=2[NH:7][C:6]1=[O:28].[C:29]1(=[O:39])[O:34][C:32](=[O:33])[C:31]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:30]12>CN(C1C=CN=CC=1)C.C(N(CC)CC)C>[C:32]([C:31]1[CH:35]=[CH:36][CH:37]=[CH:38][C:30]=1[C:29]([O:4][C@H:5]1[C@@H:11]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH2:10][C:9]2[C:20]([C:24]([F:25])([F:26])[F:27])=[CH:21][CH:22]=[CH:23][C:8]=2[NH:7][C:6]1=[O:28])=[O:39])([OH:34])=[O:33]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 6811Phthalic AnhydrideHCID 14156221HCID 14156221, compound

Product 1

HCID 14835257HCID 14835257, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
15 °C

Procedure

Under argon, to dry methylene chloride (800 ml) and triethylamine (38 ml) was added DMAP (2.17 g) and (cis)-1,3,4,5-tetrahydro-3-hydroxy-4-(4-methoxyphenyl)-6-(trifluoromethyl)-2H-1-benzazepin -2-one (62.51 g). After stirring, the so-formed suspension was cooled to about 15° C. and phthalic anhydride (39.53 g) was added. The resulting solution was warmed to room temperature and stirred for 4 hours. Upon quenching with 500 ml of dilute hydrochloric acid the layers were separated and the crystallized product from the methylene chloride layer was filtered and washed and dried in vacuo to give 84.8 g (95.4%) of the title A compound as a white crystalline solid, m.p. 161°-162° C.

Workup

  1. temperatureThe resulting solution was warmed to room temperature
  2. stirringstirred for 4 hours
  3. customUpon quenching with 500 ml of dilute hydrochloric acid the layers
  4. customwere separated
  5. filtrationthe crystallized product from the methylene chloride layer was filtered
  6. washwashed
  7. customdried in vacuo

Sources & evidence

ORD record
ord-4c3672e4071c4dfe8780115a75969915
Source dataset
uspto-grants-1990_10
Patent number
US04965356

Reaction notes

Loading…