Diisopropylethylamine → HCID 23591838, compound

HRID 1611715Notes

Reaction equation

HRID 1611715 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[C:14]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=3[Cl:28])[CH:13]=2)[CH:5]=[CH:4][C:3]=1[N+:29]([O-:31])=[O:30].CN(C(ON1N=[N:47][C:42]2[CH:43]=[CH:44][CH:45]=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:56][CH2:57][N:58](C(C)C)C(C)C>CN(C=O)C>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12]2[CH:20]=[CH:19][C:15]([C:16]([NH:58][CH2:57][CH2:56][N:47]3[CH2:42][CH2:43][CH2:44][CH2:45]3)=[O:18])=[C:14]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=3[Cl:28])[CH:13]=2)[CH:5]=[CH:4][C:3]=1[N+:29]([O-:31])=[O:30]

Participants

5

Reactant 3

HCID 81531Diisopropylethylamine2×HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2×HCID 22254163HCID 22254163, compound3×

Product 1

HCID 23591838HCID 23591838, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The amine (1.5–2.0 equivalents) is added to a stirred solution of acid 4 (1.0 eq., 25 mg), HBTU (1.5 eq.), Hünig's base (2.0 eq.) and DMF (0.4 ml). The acid 4 is pre-activated by premixed the acid 4, HBTU, Hünig's base and DMF together sequentially in this order in a vial at room temperature under argon. The reaction is stirred for 3–4 h until complete as shown by LCMS and HPLC. At times, it is necessary to add 0.25 or 0.5 equivalents more of the coupling reagents to complete the reaction. The reaction is purified by preparative HPLC. The entire reaction is injected directly onto the preparative HPLC. The purified fractions are pooled and lyophilized to give the amide 5 as a yellow powder in greater than 85% purity and in yields of 50–70%. Preparation of N-(2-{[3-(2,4-dichlorophenyl)-4-cyanophenyl]amino}ethyl)(tert-butoxy)carboxamide (6).

Workup

  1. additionto add 0.25 or 0.5 equivalents more of the coupling reagents
  2. customthe reaction
  3. customThe reaction is purified by preparative HPLC
  4. customThe entire reaction

Sources & evidence

ORD record
ord-4f430129c35747bca39dbf05c372895e
Source dataset
uspto-grants-2006_01
Patent number
US06989382B2

Reaction notes

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