Diisopropylethylamine → HCID 86691672, compound

HRID 1407038Notes

Reaction equation

HRID 1407038 reaction equation
CCN(C(C)C)C(C)C.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]2([NH:42][C:43]3[N:48]=[C:47]([O:49][CH2:50][C:51]([F:54])([F:53])[F:52])[N:46]=[C:45]([NH:55][C:56]4[CH:64]=[CH:63][C:59]([C:60](O)=[O:61])=[CH:58][CH:57]=4)[N:44]=3)[CH2:41][CH2:40]2)=[CH:35][CH:34]=1.[NH2:65][CH2:66][C:67]([CH3:78])([CH3:77])[CH2:68][NH:69][C:70](=[O:76])[O:71][C:72]([CH3:75])([CH3:74])[CH3:73]>CN(C=O)C.CCOC(C)=O>[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]2([NH:42][C:43]3[N:48]=[C:47]([O:49][CH2:50][C:51]([F:54])([F:53])[F:52])[N:46]=[C:45]([NH:55][C:56]4[CH:57]=[CH:58][C:59]([C:60]([NH:65][CH2:66][C:67]([CH3:78])([CH3:77])[CH2:68][NH:69][C:70](=[O:76])[O:71][C:72]([CH3:74])([CH3:73])[CH3:75])=[O:61])=[CH:63][CH:64]=4)[N:44]=3)[CH2:40][CH2:41]2)=[CH:35][CH:34]=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 667654164-(4-(1-(4-Chlorophenyl)cyclopropylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoic acid

Product 1

HCID 86691672HCID 86691672, compoundYield 71.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

iPr2NEt (0.266 g) and O-benzotriazol-1-yl-N,N,N′,N′-tetra-methyluronium tetrafluoroborate (0.610 g) were added into a solution of 4-(4-(1-(4-chlorophenyl)cyclopropylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoic acid (0.760 g) and tert-butyl 3-amino-2,2-dimethylpropylcarbamate (0.352 g) were dissolved in DMF (3 mL). The reaction was stirred at room temperature for 16 hrs before 200 mL of EtOAc was added. The organic phase was washed with water (2×25 mL) and brine (20 mL), dried over MgSO4, and concentrated to give crude product tert-butyl 3-(4-(4-(1-(4-chlorophenyl)cyclopropylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzamido)-2,2-dimethylpropylcarbamate (0.75 g) which was dissolved in CH2Cl2 (3 mL) and TFA (1.3 mL). After being stirred at room temperature for 16 hours, the mixture was concentrated to give a crude product, N-(3-amino-2,2-dimethylpropyl)-4-(4-(1-(4-chlorophenyl)cyclopropylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzamide (0.63 g).

Workup

  1. additionwas added
  2. washThe organic phase was washed with water (2×25 mL) and brine (20 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1771f999f1454982a328da6692464a81
Source dataset
uspto-grants-2014_12
Patent number
US08916702B2

Reaction notes

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