Diisopropylethylamine → HCID 69309534, compound

HRID 1947018Notes

Reaction equation

HRID 1947018 reaction equation
O[CH:2]1[CH2:7][CH2:6][N:5]([C:8]([CH:10]2[CH2:15][CH2:14][CH:13]([NH:16][C:17]3[N:22]=[C:21]([N:23]4[C:31]5[C:26](=[C:27]([O:32][CH2:33][CH2:34][CH2:35][S:36]([CH3:39])(=[O:38])=[O:37])[CH:28]=[CH:29][CH:30]=5)[CH:25]=[CH:24]4)[CH:20]=[CH:19][N:18]=3)[CH2:12][CH2:11]2)=[O:9])[CH2:4][CH2:3]1.[C:40]([O:44][C:45](=[O:54])[NH:46][CH2:47]C1CCNCC1)([CH3:43])([CH3:42])[CH3:41].C(N(C(C)C)CC)(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>C1COCC1>[C:40]([O:44][C:45](=[O:54])[NH:46][CH2:47][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([CH:10]2[CH2:11][CH2:12][CH:13]([NH:16][C:17]3[N:22]=[C:21]([N:23]4[C:31]5[C:26](=[C:27]([O:32][CH2:33][CH2:34][CH2:35][S:36]([CH3:39])(=[O:38])=[O:37])[CH:28]=[CH:29][CH:30]=5)[CH:25]=[CH:24]4)[CH:20]=[CH:19][N:18]=3)[CH2:14][CH2:15]2)=[O:9])[CH2:4][CH2:3]1)([CH3:43])([CH3:42])[CH3:41]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 723429Tert-butyl (piperidin-4-ylmethyl)carbamateHCID 58017084HCID 58017084, compound

Product 1

HCID 69309534HCID 69309534, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(4-hydroxy-piperidin-1-yl)-(4-{4-[4-(3-methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexyl)-methanone (0.855 g, 2.116 mM) and piperidin-4-ylmethyl-carbamic acid t-butyl ester (0.907 g, 4.232 mM) were mixed in THF (40 mL) for approximately 2 h with diisopropylethylamine (1.47 mL, 8.464 mM) and BOP (1.87 g, 4.23 mM) to yield a fine solid that was purified on an alumina column with 1-3% MeOH/CH2Cl2, dried and extracted into EtOAc to yield [1-(4-{4-[4-(3-methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarbonyl)-piperidin-4-ylmethyl]-carbamic acid t-butyl ester as a white powder upon drying in vacuo (0.856 g).

Workup

  1. customto yield a fine solid
  2. customthat was purified on an alumina column with 1-3% MeOH/CH2Cl2
  3. customdried
  4. extractionextracted into EtOAc

Sources & evidence

ORD record
ord-d430374b031d405aa967355b5e3af9f9
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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