Triethylamine → HCID 136181670, compound

HRID 720089Notes

Reaction equation

HRID 720089 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.[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][CH:32]([CH2:35][C:36](O)=[O:37])[CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23].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(Cl)Cl.CN(C)C=O.CO.CCCCCC>[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][CH:32]([CH2:35][C:36](=[O:37])[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)[CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 1512539[1-(tert-Butoxycarbonyl)piperidin-4-yl]acetic 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 136181670HCID 136181670, compoundYield 100%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolvent

Procedure

Preparation of example 30 from the title compound of Example 7 (hydrochloride) (22 mg, 0.07 mmol), 4-carboxymethyl-piperidine-1-carboxylic acid tert-butyl ester (20 mg, 0.084 mmol), triethylamine (0.015 mL, 0.105 mmol), and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (32 mg, 0.084 mmol) in CH2Cl2 (0.3 mL) and N,N-dimethylformamide (0.3 mL) was carried out analogously to Example 11. Silica gel chromatography (8:5:2 CH2Cl2:hexane:methanol), also in an analogous manner, afforded the title compound (35 mg, 0.070 mmol) as a yellow powder in 100% yield.

Sources & evidence

ORD record
ord-156ea31c326f4905adca5646d5d76076
Source dataset
uspto-grants-2006_11
Patent number
US07132533B2

Reaction notes

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