Diisopropylethylamine → HCID 67494607, compound

HRID 2047143Notes

Reaction equation

HRID 2047143 reaction equation
[CH2:1]([O:8][C@@H:9]([C:11]1[O:15][C:14](=O)[NH:13][N:12]=1)[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]1([C:23]2[N:28]=[CH:27][C:26]([C:29]3[CH:30]=[N:31][N:32]4[C:37]([N:38]([CH2:47][O:48][CH2:49][CH2:50][Si:51]([CH3:54])([CH3:53])[CH3:52])[CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:46])([CH3:45])[CH3:44])=[CH:36][C:35]([CH:55]5[CH2:60][CH2:59][NH:58][CH2:57][CH2:56]5)=[N:34][C:33]=34)=[CH:25][CH:24]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C.O>[CH2:1]([O:8][C@@H:9]([C:11]1[O:15][C:14]([N:58]2[CH2:57][CH2:56][CH:55]([C:35]3[CH:36]=[C:37]([N:38]([CH2:47][O:48][CH2:49][CH2:50][Si:51]([CH3:54])([CH3:53])[CH3:52])[CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:46])([CH3:45])[CH3:44])[N:32]4[N:31]=[CH:30][C:29]([C:26]5[CH:27]=[N:28][C:23]([C:17]6[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=6)=[CH:24][CH:25]=5)=[C:33]4[N:34]=3)[CH2:60][CH2:59]2)=[N:13][N:12]=1)[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 66733615HCID 66733615, compoundHCID 67494583HCID 67494583, compound

Product 1

HCID 67494607HCID 67494607, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of (R)-5-(1-(benzyloxy)ethyl)-1,3,4-oxadiazol-2(3H)-one (44 mg, 0.2 mmol), 3-(6-phenylpyridin-3-yl)-5-(piperidin-4-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (150 mg, 0.24 mmol) and DIEA (70 ul, 0.4 mmol) in DMF (1.4 mL) was added BOP (97 mg, 0.22 mmol) and the resulting solution was allowed to stir overnight. Water was added and was extracted with EtOAc (3×) and combined organic layers were washed with water (3×), brine once and dried (MgSO4). After concentration in vacuo the residue was purified on silica gel. Elution with EtOAc/Hexanes (0-10%) gave the title compound (142 mg, 85%).

Workup

  1. extractionwas extracted with EtOAc (3×)
  2. washwere washed with water (3×), brine once
  3. dry with materialdried (MgSO4)
  4. concentrationAfter concentration in vacuo the residue
  5. customwas purified on silica gel
  6. washElution with EtOAc/Hexanes (0-10%)

Sources & evidence

ORD record
ord-627aea2be09e4f6ea4a3b35103f6ee51
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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