Diisopropylethylamine → HCID 86636568, compound

HRID 2081129Notes

Reaction equation

HRID 2081129 reaction equation
Cl.[Cl:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][N:6]([C:12]([O:14][C@@H:15]1[CH2:19][C@@H:18]([C:20](=[O:36])[NH:21][C@:22]3([C:27](=[O:35])[NH:28][S:29]([CH:32]4[CH2:34][CH2:33]4)(=[O:31])=[O:30])[CH2:24][C@H:23]3[CH2:25][CH3:26])[NH:17][CH2:16]1)=[O:13])[CH2:7]2.[C:37]([O:41][C:42]([C@@H:44]([CH:48]1[CH2:53][CH2:52][CH2:51][CH2:50][CH2:49]1)[C:45](O)=[O:46])=[O:43])([CH3:40])([CH3:39])[CH3:38].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[CH:32]1([S:29]([NH:28][C:27]([C@@:22]2([NH:21][C:20]([C@H:18]3[N:17]([C:45](=[O:46])[C@@H:44]([C:42]([O:41][C:37]([CH3:39])([CH3:38])[CH3:40])=[O:43])[CH:48]4[CH2:53][CH2:52][CH2:51][CH2:50][CH2:49]4)[CH2:16][C@H:15]([O:14][C:12]([N:6]4[CH2:5][C:4]5[C:8](=[CH:9][CH:10]=[CH:11][C:3]=5[Cl:2])[CH2:7]4)=[O:13])[CH2:19]3)=[O:36])[CH2:24][C@H:23]2[CH2:25][CH3:26])=[O:35])(=[O:31])=[O:30])[CH2:33][CH2:34]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57463500HCID 57463500, compoundHCID 57463501HCID 57463501, compound

Product 1

HCID 86636568HCID 86636568, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A 10 mL round-bottomed flask was charged with (3R,5S)-5-(((1R,2R)-1-(cyclopropylsulfonylcarbamoyl)-2-ethylcyclopropyl)carbamoyl)pyrrolidin-3-yl 4-chloroisoindoline-2-carboxylate hydrochloride (0.150 g, 0.267 mmol), (S)-2-(tert-butoxycarbonyl)-2-cyclohexylacetic acid (82 mg, 0.32 mmol) and HATU (122 mg, 0.321 mmol) and stirred in dry DMF (1.5 mL). The solution was cooled on an ice-water bath and then treated with DIEA (0.140 mL, 0.802 mmol) by dropwise addition. The mixture was stirred at 0° C. for 1 h, then allowed to warm up and stirred at room temperature for 16 h. The reaction mixture was diluted with water (5.0 mL) resulting in the separation of a precipitate. After stirring at room temperature for about 1 hour the precipitate was collected by filtration, washed with water and dried to a cream colored solid, (195 mg, 95%). MS m/e 664 (M+−Boc).

Workup

  1. temperatureThe solution was cooled on an ice-water bath
  2. temperatureto warm up
  3. stirringstirred at room temperature for 16 h
  4. customresulting in the separation of a precipitate
  5. stirringAfter stirring at room temperature for about 1 hour the precipitate
  6. filtrationwas collected by filtration
  7. washwashed with water
  8. customdried to a cream

Sources & evidence

ORD record
ord-14f00c87dee6446894c38e83a3d6ca21
Source dataset
uspto-grants-2011_04
Patent number
US07932277B2

Reaction notes

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