Triethylamine → HCID 136141743, compound

HRID 720130Notes

Reaction equation

HRID 720130 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.[OH:22][C@H:23]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:24](O)=[O:25].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.C(OCC)C>[OH:22][C@H:23]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:24]([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)=[O:25]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 11914(-)-Mandelic 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 136141743HCID 136141743, compoundYield 56%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 21864698Diethyl ether methanolSolvent

Procedure

Preparation of example 133 from the title compound of Example 7 (hydrochloride) (46 mg, 0.147 mmol), (2R)-hydroxy(phenyl)ethanoic acid (27 mg, 0.177 mmol), triethylamine (0.061 mL, 0.44 mmol), and O-(7azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (67 mg, 0.177 mmol) in CH2Cl2 (0.4 ml) and N,N-dimethylformamide (0.4) was carried out analogously to Example 11. Silica gel chromatography (eluted with 3:1:1 hexane:ethyl acetate:ethanol), also in an analogous manner, followed by two successive triturations (ethyl acetate/diethyl ether then methanol/diethyl ether) afforded the title compound (34 mg, 0.082 mmol) as a yellow powder in 56% yield.

Workup

  1. washSilica gel chromatography (eluted with 3:1:1 hexane:ethyl acetate:ethanol)

Sources & evidence

ORD record
ord-d373f94724bb4a2a935242106f7957de
Source dataset
uspto-grants-2006_11
Patent number
US07132533B2

Reaction notes

Loading…