Diisopropylethylamine → HCID 178467961, compound

HRID 1946993Notes

Reaction equation

HRID 1946993 reaction equation
[N:1]1([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C@H:17]3[CH2:22][CH2:21][C@H:20]([C:23](O)=[O:24])[CH2:19][CH2:18]3)[N:11]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1.N[C:27]([OH:31])([CH2:29][CH3:30])[CH3:28].F[P-](F)(F)(F)(F)F.[N:39]1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C>C1COCC1.O>[OH:31][CH:27]([CH3:28])[CH2:29][CH2:30][NH:39][C:23]([C@H:20]1[CH2:21][CH2:22][C@H:17]([NH:16][C:12]2[N:11]=[C:10]([N:1]3[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[CH:3]=[N:2]3)[CH:15]=[CH:14][N:13]=2)[CH2:18][CH2:19]1)=[O:24]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 15222350HCID 15222350, compoundHCID 178525763HCID 178525763, compound

Product 1

HCID 178467961HCID 178467961, compoundYield 63.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of trans-4-(4-indazol-1-ylpyrimidin-2-ylamino)-cyclohexanecarboxylic acid (100 mg, 0.30 mmol), 2-amino-2-butanol (39.2 mg, 0.44 mmol), BOP (194.6 mg, 0.44 mmol), DIPEA (77.4 mg, 0.60 mmol) in THF (8 mL) was stirred at RT overnight. Water (20 mL) was added to the resulting suspension: the solids first dissolved, then precipitated with the addition of more water (100 mL). The precipitate was collected by filtration, washed with water and Et2O, and dried under reduced pressure to give trans-4-(4-indazol-1-yl-pyrimidin-2-ylamino)-cyclo-hexanecarboxylic acid (3-hydroxy-butyl)amide (78 mg) as white solid. MS=409 [M+H]+.

Workup

  1. dissolutionthe solids first dissolved
  2. customprecipitated with the addition of more water (100 mL)
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water and Et2O
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-0cf09f0d2c744a8f8965753a2e14ab95
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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