Triethylamine → HCID 135457474, compound

HRID 720087Notes

Reaction equation

HRID 720087 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:20](=[O:21])[NH:19][N:18]=[CH:17][C:6]3=[C:7]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[NH:8][C:9]([CH:10]=1)=[C:5]23.[CH:22]1([CH2:28][C:29](O)=[O:30])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>C(OCC)C.C(Cl)Cl.CO.CN(C)C=O>[CH:22]1([CH2:28][C:29]([NH:1][C:2]2[CH:3]=[C:4]3[C:20](=[O:21])[NH:19][N:18]=[CH:17][C:6]4=[C:7]([C:11]5[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=5)[NH:8][C:9]([CH:10]=2)=[C:5]34)=[O:30])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 21363Cyclohexaneacetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 1357740798-Amino-2-phenyl-1,5-dihydro-[1,2]diazepino[4,5,6-cd]indol-6-one

Product 1

HCID 135457474HCID 135457474, compoundYield 36.1%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Preparation of example 28 from the title compound of Example 7 (0.025 g, 0.09 mmol), Cyclohexyl-acetic acid (0.015g, 0.11 mmol), triethylamine (0.05 mL, 0.4 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (38 mg, 0.1 mmol) and N,N-dimethylformamide (0.05 M, 1.8 mL) was carried out analogously to Example 11. Silica gel chromatography (95:5 CH2Cl2/methanol) also in an analogous manner followed by diethyl ether trituration afforded the title compound (13 mg) as a yellow powder in 36% yield.

Sources & evidence

ORD record
ord-f1865023aa994e99b9d820ff7aa61943
Source dataset
uspto-grants-2006_11
Patent number
US07132533B2

Reaction notes

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