Diisopropylethylamine → HCID 67040540, compound

HRID 605403Notes

Reaction equation

HRID 605403 reaction equation
[CH:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:12]([NH:13][C:14]3[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=3[S:23][C:24]3[CH:29]=[CH:28][C:27]([NH:30][C:31]([O:33][CH3:34])=[O:32])=[CH:26][CH:25]=3)[C:17](O)=[O:18])=[N:11][CH:10]=[N:9][C:8]=2[N:35]=1)([CH3:3])[CH3:2].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[P:58]([O:71][C:72]([CH3:75])([CH3:74])[CH3:73])([O:66][C:67]([CH3:70])([CH3:69])[CH3:68])([O:60][CH2:61][C:62]([NH2:65])([CH3:64])[CH3:63])=[O:59].C(N(CC)C(C)C)(C)C>CS(C)=O>[C:72]([O:71][P:58]([O:60][CH2:61][C:62]([NH:65][C:17]([C:16]1[CH:20]=[CH:21][C:22]([S:23][C:24]2[CH:25]=[CH:26][C:27]([NH:30][C:31](=[O:32])[O:33][CH3:34])=[CH:28][CH:29]=2)=[C:14]([NH:13][C:12]2[C:7]3[CH:6]=[CH:5][C:4]([CH:1]([CH3:3])[CH3:2])=[N:35][C:8]=3[N:9]=[CH:10][N:11]=2)[CH:15]=1)=[O:18])([CH3:64])[CH3:63])([O:66][C:67]([CH3:70])([CH3:69])[CH3:68])=[O:59])([CH3:75])([CH3:74])[CH3:73]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 670408713-(7-Isopropylpyrido[2,3-d]pyrimidin-4-ylamino)-4-(4-(methoxycarbonylamino)phenylthio)benzoic acidHCID 866155662-Amino-2-methylpropyl di-tert-butyl phosphate

Product 1

HCID 67040540HCID 67040540, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a suspension of the product from Example 441D (200 mg, 0.41 mmol) and O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium tetrafluoroborate [TBTU] (187 mg, 0.57 mmol) in DMSO (2 mL) was added the product of Example 438C (178 mg, 0.57 mmol) then N,N-diisopropylethylamine (0.220 mL, 1.10 mmol) dropwise at room temperature under N2. After 2 hours the reaction was quenche with water (20 mL) and extracted with ethyl acetate (75 mL). The organic layer was washed sequentially with water (3×) and saturated aqueous NaHCO3, dried over MgSO4, and concentrated. The residue was purified by silica gel column chromatography eluting with ethyl acetate to give the title compound as a pale yellow amorphous solid (245 mg., 79%).

Workup

  1. customdropwise at room temperature
  2. customAfter 2 hours the reaction was quenche with water (20 mL)
  3. extractionextracted with ethyl acetate (75 mL)
  4. washThe organic layer was washed sequentially with water (3×) and saturated aqueous NaHCO3
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-fdb124647d4845d39692774b24fd1d82
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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