4-Methylmorpholine → HCID 49842017, compound

HRID 1627119Notes

Reaction equation

HRID 1627119 reaction equation
[CH:1]1([NH:6][C:7](=[O:27])[C@H:8]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][N:18]=[C:17]3[NH:21][CH:22]=[C:23]([C:24]([OH:26])=O)[C:16]=23)[C@H:9]([CH3:12])[CH2:10][CH3:11])[CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>C1COCC1>[CH:1]1([NH:6][C:7](=[O:27])[C@H:8]([N:13]2[C:24](=[O:26])[C:23]3=[CH:22][NH:21][C:17]4[C:16]3=[C:15]([CH:20]=[CH:19][N:18]=4)[CH2:14]2)[C@H:9]([CH3:12])[CH2:10][CH3:11])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

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 67223917HCID 67223917, compound

Product 1

HCID 49842017HCID 49842017, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a manner similar to Step C of Example 19, 4-(((2R,3R)-1-(cyclopentylamino)-3-methyl-1-oxopentan-2-ylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid was cyclized in a mixture of THF (2 mL), HATU (112 mg, 0.296 mmol) and 4-methylmorpholine (37.4 mg, 0.370 mmol) and the resulting product was purified via preparative mass trigger LC-MS (AcCN/H2O, 5-50%). The fractions were collected, concentrated, and dried in vacuo to afford the title compound as a yellow oil (32 mg, 37% from Step A starting material). 1H NMR (400 MHz, CD3OD) δ 0.61-0.72 (m, 2 H) 0.90-1.06 (m, 5 H) 1.37-1.66 (m, 7 H) 1.66-1.77 (m, 2 H) 1.77-1.99 (m, 4 H) 3.98-4.22 (m, 1 H) 4.85-4.97 (m, 2 H) 5.21 (d, J=9.35 Hz, 1 H). [M+H] calc'd for C20H26N4O2, 355; found, 355.5.

Workup

  1. customthe resulting product was purified via preparative mass trigger LC-MS (AcCN/H2O, 5-50%)
  2. customThe fractions were collected
  3. concentrationconcentrated
  4. customdried in vacuo

Sources & evidence

ORD record
ord-a699ab8bea244aba8d1516e9e0cbdb19
Source dataset
uspto-grants-2014_07
Patent number
US08785429B2

Reaction notes

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