Diisopropylethylamine → HCID 178455274, compound

HRID 2169321Notes

Reaction equation

HRID 2169321 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:28]([OH:30])=O)=[N:11][C:12]([CH2:16][C:17]2([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:21][CH2:20][CH2:19][CH2:18]2)=[N:13][C:14]=1[OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si:31]([O:38][CH2:39][CH2:40][NH:41][CH:42]1[CH2:46][CH2:45][CH2:44][CH2:43]1)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32].C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O.O>[Si:31]([O:38][CH2:39][CH2:40][N:41]([CH:42]1[CH2:43][CH2:44][CH2:45][CH2:46]1)[C:28]([C:10]1[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:14]([OH:15])[N:13]=[C:12]([CH2:16][C:17]2([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:21][CH2:20][CH2:19][CH2:18]2)[N:11]=1)=[O:30])([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32]

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 86725959[2-(Tert-butyl-dimethylsilanyloxy)-ethyl]-cyclopentylamineHCID 178524866HCID 178524866, compound

Product 1

HCID 178455274HCID 178455274, compoundYield 62.28%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution mixture of 5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid (283) (100 mg, 0.25 mmol) and [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-cyclopentyl-amine (8e) (72 mg, 0.29 mmol) in dimethylformamide (2.5 mL) were added N,N-diisopropylethylamine (0.1 mL, 0.74 mmol) and HATU (141 mg, 0.37 mmol). Stirring was continued at room temperature for 20 h, whereafter water (25 mL) was added and the mixture extracted with ethyl acetate (3×20 mL). The combined organic part was washed with water (3×50 mL) and brine (2×30 mL) and dried and concentrated. The crude product was purified by Combi-Flash column (eluted at 20-30% ethyl acetate in hexane) to get 5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-cyclopentyl-amide (288) (97 mg, 62.28%) as a light yellow sticky solid.

Workup

  1. additionwas added
  2. extractionthe mixture extracted with ethyl acetate (3×20 mL)
  3. washThe combined organic part was washed with water (3×50 mL) and brine (2×30 mL)
  4. customdried
  5. concentrationconcentrated
  6. customThe crude product was purified by Combi-Flash column (eluted at 20-30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-97eded13c0e24a8184a8e1f18f11e70f
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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