Acetic Acid → HCID 86707708, compound

HRID 1408959Notes

Reaction equation

HRID 1408959 reaction equation
[NH2:1][C@@:2]1([CH3:30])[CH2:6][CH2:5][C@@H:4]([NH:7][C:8]2[C:9]3[N:10]([CH:17]=[C:18]([C:20]4[CH:25]=[CH:24][C:23]([CH2:26][NH2:27])=[CH:22][CH:21]=4)[CH:19]=3)[N:11]=[CH:12][C:13]=2[C:14]([NH2:16])=[O:15])[C:3]1([CH3:29])[CH3:28].[C:31]([OH:34])(=O)[CH3:32].F[P-](F)(F)(F)(F)F.N1([O:51][P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN([CH:68]([CH3:70])C)C(C)C>CN(C=O)C>[C:68]([NH:27][CH2:26][C:23]1[CH:22]=[CH:21][C:20]([C:18]2[CH:19]=[C:9]3[C:8]([NH:7][C@@H:4]4[CH2:5][CH2:6][C@@:2]([NH:1][C:31](=[O:34])[CH3:32])([CH3:30])[C:3]4([CH3:29])[CH3:28])=[C:13]([C:14]([NH2:16])=[O:15])[CH:12]=[N:11][N:10]3[CH:17]=2)=[CH:25][CH:24]=1)(=[O:51])[CH3:70]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 86707709HCID 86707709, compound

Product 1

HCID 86707708HCID 86707708, compoundYield 40.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-((1R,3S)-3-amino-2,2,3-trimethylcyclopentylamino)-6-(4-(aminomethyl)phenyl)pyrrolo[1,2-b]pyridazine-3-carboxamide (Example 234, 8 mg, 0.020 mmol), acetic acid (1.8 mg, 0.03 mmol), BOP (1.3 mg, 0.022 mmol) and DIPEA (6.35 mg, 0.05 mmol) in DMF (0.5 mL) was stirred at rt for 2 h. The reaction was purified by preparative HPLC to afford the title compound (4 mg, 38% yield). LCMS: 491.32 (M+H); HPLC (condition B): retention time=3.51 min; 1H NMR (CDCl3, 400 MHz) δ 7.95 (s, 1H), 7.78 (s, 1H), 7.51 (m, 2H), 7.29 (m, 2H), 7.00 (m, 1H), 4.46 (M, 1H), 4.37 (s, 2H), 2.34 (m, 2H), 1.97 (m, 6H), 1.72 (m, 1H), 3.28 (s, 3H), 1.06 (s, 6H).

Workup

  1. customThe reaction was purified by preparative HPLC

Sources & evidence

ORD record
ord-43e3fcb5a00a467a87da5cc51cd68ade
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

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