Triethylamine → HCID 135531290, compound

HRID 720104Notes

Reaction equation

HRID 720104 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]([N:25]1[CH2:30][CH2:29][CH:28]([C:31](O)=[O:32])[CH2:27][CH2:26]1)(=[O: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>CN(C)C=O.C(Cl)Cl.CO>[C:22]([N:25]1[CH2:26][CH2:27][CH:28]([C:31]([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:32])[CH2:29][CH2:30]1)(=[O:24])[CH3:23]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 1172551-Acetylpiperidine-4-carboxylic 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 135531290HCID 135531290, compoundYield 25.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent3×HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

Preparation of example 48 from the title compound of Example 7 (30 mg, 0.11 mmol), 1-acetylpiperidine-4-carboxylic acid (28 mg, 0.16 mmol), triethylamine (0.076 mL, 0.55 mmol), and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (62 mg, 0.16 mmol) in N,N-dimethylformamide (1.5 mL) was carried out analogously to Example 11. Silica gel chromatography (3% methanol in CH2Cl2 increasing to 6% methanol in CH2Cl2), also in an analogous manner, followed by methanol trituration afforded the title compound (12 mg, 0.028 mmol) as a yellow powder in 25% yield.

Sources & evidence

ORD record
ord-6ce40f84a1094ba3b90dc285ba6ea0a1
Source dataset
uspto-grants-2006_11
Patent number
US07132533B2

Reaction notes

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