Acetic Anhydride → 4-(((3S)-1-acetyl-3-piperidinyl)amino)-6-phenylpyrrolo[1,2-b]pyridazine-3-carboxamide

HRID 877727Notes

Reaction equation

HRID 877727 reaction equation
[C:1]([C:4]1[CH:9]=[N:8][N:7]2[CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:12]=[C:6]2[C:5]=1[NH:19][C@H:20]1[CH2:25][CH2:24][CH2:23][N:22]([C:26]([O:28]C(C)(C)C)=O)[CH2:21]1)(=[O:3])[NH2:2].[C:33](OC(=O)C)(=O)C.CCN(C(C)C)C(C)C>C(Cl)Cl>[C:26]([N:22]1[CH2:23][CH2:24][CH2:25][C@H:20]([NH:19][C:5]2[C:6]3[N:7]([CH:10]=[C:11]([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH:12]=3)[N:8]=[CH:9][C:4]=2[C:1]([NH2:2])=[O:3])[CH2:21]1)(=[O:28])[CH3:33]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 68291570(S)-tert-butyl 3-(3-carbamoyl-6-phenylpyrrolo[1,2-b]pyridazin-4-ylamino)piperidine-1-carboxylate

Product 1

HCID 682914384-(((3S)-1-acetyl-3-piperidinyl)amino)-6-phenylpyrrolo[1,2-b]pyridazine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of (S)-6-phenyl-4-(piperidin-3-ylamino)pyrrolo[1,2-b]pyridazine-3-carboxamide hydrochloride salt (Example 44, 12.2 mg, 0.033 mmol) in CH2Cl2 (0.3 mL) was added acetic anhydride (3.72 μL, 0.04 mmol) followed by DIPEA (0.017 mL, 0.1 mmol). The reaction was stirred for 1 h at which time the starting material had been consumed as judged by HPLC. The solvents were removed and the product purified via reverse phase preparative HPLC. LCMS: 378 (M+H)+; HPLC (conditions E): retention time=7.41 min; 1H NMR (MeOD, 400 MHz) δ 8.17 (d, J=13 Hz, 1H), 7.97 (dd, J=1.7, 12.3 Hz, 1H), 7.75 (m, 3H), 7.40 (m, 3H), 7.27 (m, 1H), 4.38 (m, 1H), 3.83-3.94 (m, 2H), 3.42 (m, 2H), 2.21 (s, 3H), 1.98 (m, 1H), 1.87 (m, 1H), 1.75 (m, 1H).

Workup

  1. customhad been consumed
  2. customThe solvents were removed
  3. customthe product purified via reverse phase preparative HPLC

Sources & evidence

ORD record
ord-8578a0a006fc45c39bb2a44af5512400
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

Loading…