4-Methylmorpholine → (R)-benzyl 2-(6-chloro-3-oxo-1-tosylpyrrolo[4,3,2-de][2,6]naphthyridin-4(1H,3H,5H)-yl)-3,3-dimethylbutanoate

HRID 1968248Notes

Reaction equation

HRID 1968248 reaction equation
[CH2:1]([O:8][C:9](=[O:40])[C@H:10]([NH:15][CH2:16][C:17]1[C:22]([Cl:23])=[CH:21][N:20]=[C:19]2[N:24]([S:30]([C:33]3[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=3)(=[O:32])=[O:31])[CH:25]=[C:26]([C:27](O)=[O:28])[C:18]=12)[C:11]([CH3:14])([CH3:13])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>>[Cl:23][C:22]1[C:17]2[CH2:16][N:15]([C@H:10]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:40])[C:27](=[O:28])[C:26]3=[CH:25][N:24]([S:30]([C:33]4[CH:34]=[CH:35][C:36]([CH3:37])=[CH:38][CH:39]=4)(=[O:32])=[O:31])[C:19]([C:18]=23)=[N:20][CH:21]=1

Participants

4

Reactant 3

HCID 79724-MethylmorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58293507HCID 58293507, compound

Product 1

HCID 58293527(R)-benzyl 2-(6-chloro-3-oxo-1-tosylpyrrolo[4,3,2-de][2,6]naphthyridin-4(1H,3H,5H)-yl)-3,3-dimethylbutanoate

Procedure

Crude (R)-4-((1-(benzyloxy)-3,3-dimethyl-1-oxobutan-2-ylamino)methyl)-5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid was heated in HATU (124 mg, 0.326 mmol) and 4-methylmorpholine (82 mg, 0.814 mmol) at reflux for 3 h. The reaction mixture was subsequently concentrated and dried in vacuo to afford the title compound. [M+H] calc'd for C29H28ClN3O5S, 566; found, 566.0.

Workup

  1. concentrationThe reaction mixture was subsequently concentrated
  2. customdried in vacuo

Sources & evidence

ORD record
ord-af51df8ee55d403c9ff7360982f1b6dd
Source dataset
uspto-grants-2013_04
Patent number
US08420816B2

Reaction notes

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