Diisopropylethylamine → HCID 67513765, compound

HRID 2273594Notes

Reaction equation

HRID 2273594 reaction equation
F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[CH:25]([N:28]1[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[N:30]=[C:29]1[NH:37][C:38]1[CH:46]=[CH:45][C:41]([C:42]([OH:44])=O)=[CH:40][CH:39]=1)([CH3:27])[CH3:26].[NH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=1[NH:54][C:55](=[O:61])[O:56][C:57]([CH3:60])([CH3:59])[CH3:58].C(N(CC)C(C)C)(C)C>>[CH:25]([N:28]1[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[N:30]=[C:29]1[NH:37][C:38]1[CH:39]=[CH:40][C:41]([C:42]([NH:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=2[NH:54][C:55](=[O:61])[O:56][C:57]([CH3:59])([CH3:58])[CH3:60])=[O:44])=[CH:45][CH:46]=1)([CH3:26])[CH3:27]

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 676311N-(tert-Butoxycarbonyl)-1,2-phenylenediamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 675138974-(1-isopropyl-1H-benzo[d]imidazol-2-ylamino)benzoic acid

Product 1

HCID 67513765HCID 67513765, compoundYield 91.9%

Procedure

2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU, 62 mg, 0.16 mmol) was added to a solution of 4-(1-isopropyl-1H-benzo[d]imidazol-2-ylamino)benzoic acid (40 mg, 0.13 mmol), tert-butyl 2-aminophenylcarbamate (34 mg, 0.16 mmol) and N,N-diisopropylethylamine (0.047 mL, 0.27 mmol. The reaction may be stirred at room temperature for an appropriate time period such as 2 hrs and quenched by water. The mixture may be extracted with any appropriate agent, such as ethyl acetate, and concentrated. The residue may be purified by any appropriate method, including Biotage column chromatography to give tert-butyl 2-(4-(1-isopropyl-1H-benzo[d]imidazol-2-ylamino)benzamido)phenylcarbamate (58 mg)

Workup

  1. customThe reaction
  2. customquenched by water
  3. extractionThe mixture may be extracted with any appropriate agent, such as ethyl acetate
  4. concentrationconcentrated
  5. customThe residue may be purified by any appropriate method

Sources & evidence

ORD record
ord-9852738960334bcbbe5846df0c6f0dc9
Source dataset
uspto-grants-2015_09
Patent number
US09125901B2

Reaction notes

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