Triethylamine → HCID 136181617, compound

HRID 720079Notes

Reaction equation

HRID 720079 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]([CH2:31][C:32](O)=[O:33])[CH3:30])=[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.C(OCC)C.CO.CCCCCC>[C:22]([O:26][C:27](=[O:28])[N:29]([CH3:30])[CH2:31][C:32](=[O:33])[NH: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:12]=[CH:13][CH:14]=[CH:15][CH:16]=4)[NH:8][C:9]([CH:10]=1)=[C:5]23)([CH3:25])([CH3:24])[CH3:23]

Participants

10

Reactant 4

HCID 8471TriethylamineHCID 83692Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-HCID 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 136181617HCID 136181617, compoundYield 96.9%

Reagents, catalysts & solvents 5

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolvent

Procedure

Preparation of example 19 from the title compound of Example 7 (hydrochloride) (18 mg, 0.065 mmol), (tert-butoxycarbonyl-methyl-amino)-acetic acid (12 mg, 0.065 mmol), triethylamine (0.012 mL, 0.085 mmol), and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (27 mg, 0.072 mmol) in CH2Cl2 (0.5 mL) and N,N-dimethylformamide (0.5 mL) was carried out analogously to Example 11. Silica gel chromatography (10:9:1 hexane:CH2Cl2:methanol), also in an analogous manner, followed by diethyl ether trituration afforded the title compound (28 mg, 0.063 mmol) as a yellow powder in 96% yield.

Sources & evidence

ORD record
ord-2f6086df291b4a2cae570c4fe991b7ce
Source dataset
uspto-grants-2006_11
Patent number
US07132533B2

Reaction notes

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