Diisopropylethylamine → HCID 86645949, compound
Reaction equation
[C:1]([O:12][CH3:13])(=[O:11])[C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([O-:7])=O)[CH:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[NH2:47][C:48]1[CH:53]=[CH:52][C:51]([CH:54]([CH3:68])[C:55]([C:61]2[CH:66]=[CH:65][N:64]=[C:63]([Cl:67])[CH:62]=2)([OH:60])[C:56]([F:59])([F:58])[F:57])=[C:50]([Cl:69])[CH:49]=1>CN(C=O)C>[CH3:13][O:12][C:1](=[O:11])[C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([NH:47][C:48]2[CH:53]=[CH:52][C:51]([CH:54]([CH3:68])[C:55]([C:61]3[CH:66]=[CH:65][N:64]=[C:63]([Cl:67])[CH:62]=3)([OH:60])[C:56]([F:57])([F:58])[F:59])=[C:50]([Cl:69])[CH:49]=2)=[O:7])[CH:3]=1Participants
6
Reactant 4
HCID 81531Diisopropylethylamine2×
HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)
HCID 69512791,3-Benzenedicarboxylic acid, monomethyl ester2×
HCID 866291093-(4-Amino-2-chloro-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-olProduct 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
Monomethyl isophthalate (CAS Reg. No. 1877-71-0, 22 mg), HBTU (CAS Reg. No. 94790-37-1, 62 mg), and N,N-diisopropyl ethyl amine (0.06 ml) were added to a solution of 3-(4-amino-2-chloro-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-ol (Example 60 step 4, 40 mg) in DMF (2 ml). The mixture was stirred overnight at room temperature, 1 h at 50° C., and then 1 h at 80° C. Additional monomethyl isophthalate (CAS Reg. No. 1877-71-0, 20 mg) and N,N-diisopropyl ethyl amine (0.02 ml) were added. The mixture was purified by prep. HPLC (C18-column, solvent gradient 30-98% CH3CN in 0.1% HCOOH[aq]) to give the title compound (13 mg) as a light yellow foam. MS (m/e)=527.0 [M+H+].
Workup
- custom1 h
- customat 80° C
- customThe mixture was purified by prep
Sources & evidence
- ORD record
- ord-c8558586ee734e1e9b7cc025ffa061e2
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08138189B2
Reaction notes
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