Dimethylformamide → HCID 68683795, compound

HRID 2234328Notes

Reaction equation

[CH:1]1([N:6]2[CH2:16][C:15]([CH3:18])([CH3:17])[C:14](=[O:19])[N:13]([CH3:20])[C:12]3[C:7]2=[N:8][C:9]([NH:21][C:22]2[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][C:23]=2[Cl:31])=[N:10][CH:11]=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.C[CH2:33][N:34]([CH:38]([CH3:40])[CH3:39])[CH:35]([CH3:37])[CH3:36].[CH3:41][N:42](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:65]N(C=O)C>>[Cl:31][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][C:22]=1[NH:21][C:9]1[N:10]=[CH:11][C:12]2[N:13]([CH3:20])[C:14](=[O:19])[C:15]3([CH2:17][CH2:18]3)[CH2:16][N:6]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[C:7]=2[N:8]=1)[C:26]([NH:42][CH:41]1[CH2:37][C@H:35]2[N:34]([CH3:33])[C@H:38]([CH2:40][CH2:65][CH2:36]2)[CH2:39]1)=[O:27]

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 81531Diisopropylethylamine

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

HCID 68683735HCID 68683735, compound2×

Product 1

HCID 68683795HCID 68683795, compound

Procedure

4-[(2-cyclopentyl-4,4,6-trimethyl-5-oxo-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-10-yl)amino]-3-chloro-benzoic acid (Intermediate 253; 52 mg, 0.12 mmol) was suspended in DMF (4 mL). DIPEA (62 ul, 0.35 mmol) was added to give a straw coloured solution. Endo-9-methyl-9-azabicyclo[3,3,1]-nonan-3-amine (Chempacific; 26 mg, 0.16 mmol) was added, followed by HATU (67 mg, 0.17 mmol) and the resultant mixture was stirred at ambient temperature overnight.

Workup

customto give a straw coloured solution

Sources & evidence

ORD record: ord-5245105eda834888a4978d56431fd799
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709471B2

Reaction notes

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