Diisopropylethylamine → HCID 178461982, compound

HRID 42348Notes

Reaction equation

HRID 42348 reaction equation
Cl[C:2]1[N:3]=[C:4]([OH:19])[C:5]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1.[NH2:20][C@@H:21]([C:23]1[CH:28]=[CH:27][C:26]([S:29]([NH:32][C:33]([CH3:36])([CH3:35])[CH3:34])(=[O:31])=[O:30])=[CH:25][CH:24]=1)[CH3:22].CCN(C(C)C)C(C)C.O.C(#N)C>CN1C(=O)CCC1>[C:33]([NH:32][S:29]([C:26]1[CH:25]=[CH:24][C:23]([C@H:21]([NH:20][C:2]2[N:3]=[C:4]([OH:19])[C:5]3[N:11]=[C:10]([C:12]4[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=4)[CH:9]=[CH:8][C:6]=3[N:7]=2)[CH3:22])=[CH:28][CH:27]=1)(=[O:31])=[O:30])([CH3:36])([CH3:34])[CH3:35]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 18373917Acetonitrile--water (1/1)HCID 28714635(R)-4-(1-aminoethyl)-N-tert-butylbenzenesulfonamideHCID 178517814HCID 178517814, compound

Product 1

HCID 178461982HCID 178461982, compoundYield 162.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-chloro-6-(4-fluorophenyl)pyrido[3,2-d]pyrimidin-4-ol (377 mg), (R)-4-(1-aminoethyl)-N-tert-butylbenzenesulfonamide (456 mg) and DIEA (243 ml) in NMP (4 ml) was heated at 120° C. overnight. The reaction mixture was then added to H2O/ACN (9:1) with vigorous stirring and extracted with EtOAc. The organic layer was dried and concentrated to give 1.1 g crude (R)—N-tert-butyl-4-(1-(6-(4 fluorophenyl)-4-hydroxypyrido[3,2-d]pyrimidin-2-ylamino)ethyl)benzenesulfonamide as golden brown oil, which was used in the next step without purification.

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d2f8bc44125c4c279e602f75ded9a355
Source dataset
uspto-grants-2013_09
Patent number
US08536187B2

Reaction notes

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