Diisopropylethylamine → HCID 69309770, compound

HRID 1947021Notes

Reaction equation

HRID 1947021 reaction equation
[Si:1]([O:8][CH:9]1[CH2:13][CH2:12][N:11]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH:16]=[CH:17][N:18]3[C:23]2[CH:28]=[CH:27][N:26]=[C:25](S(C)(=O)=O)[N:24]=2)[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Cl.[NH2:34][CH:35]1[CH2:40][CH2:39][CH:38]([NH:41][S:42]([CH3:45])(=[O:44])=[O:43])[CH2:37][CH2:36]1.CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[Si:1]([O:8][CH:9]1[CH2:13][CH2:12][N:11]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH:16]=[CH:17][N:18]3[C:23]2[CH:28]=[CH:27][N:26]=[C:25]([NH:34][CH:35]3[CH2:40][CH2:39][CH:38]([NH:41][S:42]([CH3:45])(=[O:44])=[O:43])[CH2:37][CH2:36]3)[N:24]=2)[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 54594800N-(4-aminocyclohexyl)methanesulfonamide hydrochlorideHCID 69307215HCID 69307215, compound

Product 1

HCID 69309770HCID 69309770, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

4-[3-(t-Butyl-dimethylsilyloxy)pyrrolidin-1-yl]-1-(2-methylsulfonyl-pyrimidin-4-yl)-1H-indole (about 160 mg, 0.35 mmol), N-(4-amino-cyclohexyl)-methanesulfonamide hydro-chloride (743 mg, 3.255 mmol) and DIEA (0.169 mL, 4.32 mmol) were mixed in NMP (7 mL) under Ar at 130° C. for 2.5 h. The reaction mixture was washed with NH4Cl/H2O and extracted into EtOAc (6×15 mL), and further washed with H2O (6×30 mL). The solvent was removed in vacuo to yield N-[4-(4-{4-[3-(t-butyl-dimethylsilanyloxy)-pyrrolidin-1-yl]-indol-1-yl}-pyrimidin-2-ylamino)-cyclohexyl]-methanesulfonamide (150 mg).

Workup

  1. washThe reaction mixture was washed with NH4Cl/H2O
  2. extractionextracted into EtOAc (6×15 mL)
  3. washfurther washed with H2O (6×30 mL)
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f37f89f615964b2386e48d4948a64835
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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