Diisopropylethylamine → HCID 58275536, compound

HRID 42350Notes

Reaction equation

HRID 42350 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]=[C:13]([NH:19][C@@H:20]([C:22]4[CH:27]=[CH:26][C:25]([S:28]([NH2:31])(=[O:30])=[O:29])=[CH:24][CH:23]=4)[CH3:21])[N:14]=[C:15]([OH:18])[C:16]=3[N:17]=2)=[CH:4][CH:3]=1.F[P-](F)(F)(F)(F)F.[N:39]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][C:42]=2[N:41]=[N:40]1.CCN(C(C)C)C(C)C>C1COCC1>[N:39]1([O:18][C:15]2[C:16]3[N:17]=[C:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)[CH:9]=[CH:10][C:11]=3[N:12]=[C:13]([NH:19][C@@H:20]([C:22]3[CH:27]=[CH:26][C:25]([S:28]([NH2:31])(=[O:29])=[O:30])=[CH:24][CH:23]=3)[CH3:21])[N:14]=2)[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][C:42]=2[N:41]=[N:40]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 178461981HCID 178461981, compound

Product 1

HCID 58275536HCID 58275536, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (R)-4-(1-(6-(4-fluorophenyl)-4-hydroxypyrido[3,2-d]pyrimidin-2-ylamino)ethyl)benzenesulfonamide (200 mg), BOP (479 mg) and DIEA (314 μl) in THF (10 ml) was stirred at room temperature overnight. The reaction mixture was concentrated and purified by silicon gel column chromatography (eluting with EtOAc/CH2Cl2) to provide (R)-4-(1-(4-(1H-benzo[d][1,2,3]triazol-1-yloxy)-6-(4-fluorophenyl)pyrido[3,2-d]pyrimidin-2-ylamino)ethyl)benzenesulfonamide as a yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by silicon gel column chromatography (eluting with EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-8daa3d24dc0f49a8a95a0cbfeb500c2b
Source dataset
uspto-grants-2013_09
Patent number
US08536187B2

Reaction notes

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