Diisopropylethylamine → HCID 90101928, compound

HRID 1485652Notes

Reaction equation

HRID 1485652 reaction equation
[Cl:1][CH2:2][C:3](=[CH2:36])[CH2:4][O:5][C:6]1[CH:35]=[CH:34][C:9]([CH2:10][NH:11][C:12]2[N:17]=[C:16]([O:18][CH2:19][C:20]([F:23])([F:22])[F:21])[N:15]=[C:14]([NH:24][C:25]3[CH:33]=[CH:32][C:28]([C:29](O)=[O:30])=[CH:27][CH:26]=3)[N:13]=2)=[CH:8][CH:7]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[C:59]([O:63][C:64](=[O:72])[NH:65][CH2:66][C:67]([CH3:71])([CH3:70])[CH2:68][NH2:69])([CH3:62])([CH3:61])[CH3:60].CCN(C(C)C)C(C)C>CN1C(=O)CCC1.O>[Cl:1][CH2:2][C:3](=[CH2:36])[CH2:4][O:5][C:6]1[CH:35]=[CH:34][C:9]([CH2:10][NH:11][C:12]2[N:17]=[C:16]([O:18][CH2:19][C:20]([F:23])([F:21])[F:22])[N:15]=[C:14]([NH:24][C:25]3[CH:26]=[CH:27][C:28]([C:29]([NH:69][CH2:68][C:67]([CH3:71])([CH3:70])[CH2:66][NH:65][C:64](=[O:72])[O:63][C:59]([CH3:61])([CH3:60])[CH3:62])=[O:30])=[CH:32][CH:33]=3)[N:13]=2)=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 4114359tert-butyl N-(3-amino-2,2-dimethylpropyl)carbamateHCID 90101345HCID 90101345, compound

Product 1

HCID 90101928HCID 90101928, compoundYield 67.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 4-((4-((4-((2-(chloromethyl)allyl)oxy)benzyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)benzoic acid (1.1 g) and TBTU (0.74 g) in NMP (10 mL) was added tert-butyl(3-amino-2,2-dimethylpropyl)carbamate (0.51 g) and DIPEA (1.47 mL). After stirring at room temperature for 2 hours, the mixture was diluted with 100 mL of water and extracted with EtOAc (2×150 mL). The organic layer were combined, washed with brine (100 mL), dried over MgSO4 and concentrated. The residue was purified by silica gel column to give tert-butyl 3-(4-(4-(4-(2-(chloromethyl)allyloxy)benzylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzamido)-2,2-dimethylpropylcarbamate (1 g).

Workup

  1. extractionextracted with EtOAc (2×150 mL)
  2. washwashed with brine (100 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column

Sources & evidence

ORD record
ord-756b81d813f6421d81e9505d53c60c50
Source dataset
uspto-grants-2016_08
Patent number
US09422311B2

Reaction notes

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