Diisopropylethylamine → HCID 59743517, compound

HRID 1947060Notes

Reaction equation

HRID 1947060 reaction equation
[C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][CH:20]3[CH2:25][CH2:24][CH:23]([C:26](O)=[O:27])[CH2:22][CH2:21]3)[N:14]=2)[CH:5]=1)(=[O:3])[NH2:2].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.[CH3:65][N:66]([CH:68]1[CH2:73][CH2:72][NH:71][CH2:70][CH2:69]1)[CH3:67]>C1COCC1>[CH3:65][N:66]([CH3:67])[CH:68]1[CH2:73][CH2:72][N:71]([C:26]([CH:23]2[CH2:24][CH2:25][CH:20]([NH:19][C:15]3[N:14]=[C:13]([N:6]4[C:7]5[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=5)[C:4]([C:1]([NH2:2])=[O:3])=[CH:5]4)[CH:18]=[CH:17][N:16]=3)[CH2:21][CH2:22]2)=[O:27])[CH2:70][CH2:69]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 417391N,N-Dimethylpiperidin-4-amineHCID 69311851HCID 69311851, compound

Product 1

HCID 59743517HCID 59743517, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 4-[4-(3-carbamoyl-indol-1-yl)-pyrimidin-2-ylamino]-cyclo-hexanecarboxylic acid (150 mg, 0.395 mmol) in THF was added BOP, followed by Hünig's base (103 μL, 0.593 mmol), the mixture stirred for 10 min, and 4-(N,N-dimethylamino)-piperidine (76 mg, 0.593 mmol) was added and stirred for 6 days at RT. The resulting white solid was filtered off, washed with dry THF (20 mL) and DCM (30 mL), and air-dried overnight. The product was purified by prep-TLC using 5% MeOH/DCM+NH4OH, and dried under vacuum to provide 1-{2-[4-(4-dimethylamino-piperidine-1-carbonyl)-cyclohexylamino]-pyrimidin-4-yl}-1H-indole-3-carboxylic acid amide (78 mg, 40.3% yield) as a yellow solid (Compound 295).

Workup

  1. stirringstirred for 6 days at RT
  2. filtrationThe resulting white solid was filtered off
  3. washwashed with dry THF (20 mL) and DCM (30 mL)
  4. customair-dried overnight
  5. customThe product was purified
  6. customdried under vacuum

Sources & evidence

ORD record
ord-b7b585c5a77b4cad90da0b41ec9e4c3a
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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