Triethylamine → HCID 58550835, compound

HRID 2204281Notes

Reaction equation

HRID 2204281 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:28]3[C:29]([C:32](O)=[O:33])=[CH:30][CH:31]=[C:27]3[C:8]3([CH2:13][CH2:12][N:11]([C:14](=[O:26])[C:15]4[CH:20]=[CH:19][C:18]([O:21][CH:22]([CH3:24])[CH3:23])=[C:17]([CH3:25])[CH:16]=4)[CH2:10][CH2:9]3)[O:7][C:6]=2[CH:35]=1.Cl.CN.C[CH2:40][N:41](CC)CC.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:28]3[C:29]([C:32]([NH:41][CH3:40])=[O:33])=[CH:30][CH:31]=[C:27]3[C:8]3([CH2:13][CH2:12][N:11]([C:14](=[O:26])[C:15]4[CH:20]=[CH:19][C:18]([O:21][CH:22]([CH3:23])[CH3:24])=[C:17]([CH3:25])[CH:16]=4)[CH2:10][CH2:9]3)[O:7][C:6]=2[CH:35]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 6364545Methylamine hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67467458HCID 67467458, compound

Product 1

HCID 58550835HCID 58550835, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-Chloro-1′-(4-isopropoxy-3-methylbenzoyl)spiro[benzo[b]-pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1-carboxylic acid (17 mg, 0.034 mmol), methanamine hydrochloride (2.3 mg, 0.034 mmol), and Et3N (19 μL, 0.14 mmol) were taken up in dry dichloromethane (0.5 mL). HATU (13 mg, 0.034 mmol) was added and the mixture was allowed to stir for 15 min at room temperature. The mixture was purified by prep-HPLC to provide 7-chloro-1′-(4-isopropoxy-3-methylbenzoyl)-N-methylspiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1-carboxamide. ESI-MS m/z calc. 507.2, found 508.0 (M+1)+. Retention time: 1.92 minutes (3 min run).

Workup

  1. customThe mixture was purified by prep-HPLC

Sources & evidence

ORD record
ord-9ef618f58ed249f88cb101bdeb3f3131
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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