Triethylamine → HCID 25253818, compound

HRID 1396091Notes

Reaction equation

HRID 1396091 reaction equation
[NH2:1][C:2]1[C:17]2[C:16](=[O:18])[C:15]([C:19]([OH:21])=[O:20])=[CH:14][N:7]3[CH2:8][C:9]4([CH2:13][CH2:12][CH2:11]4)[O:10][C:5]([C:6]=23)=[C:4](F)[C:3]=1[F:23].C(N(CC)CC)C.[N:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[NH:37][CH2:38][CH2:39][NH2:40]>CS(C)=O>[NH2:1][C:2]1[C:17]2[C:16](=[O:18])[C:15]([C:19]([OH:21])=[O:20])=[CH:14][N:7]3[CH2:8][C:9]4([CH2:13][CH2:12][CH2:11]4)[O:10][C:5]([C:6]=23)=[C:4]([NH:40][CH2:39][CH2:38][NH:37][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][N:31]=2)[C:3]=1[F:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 410428N~1~-(Pyridin-2-yl)ethane-1,2-diamineHCID 58134829HCID 58134829, compound

Product 1

HCID 25253818HCID 25253818, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 8′-amino-9′,10′-difluoro-7′-oxospiro[cyclobutane-1,2′(3′H)-[7H]pyrido[1,2,3-de][1,4]benzoxazine]-6′-carboxylic acid (200 mg, 0.621 mmol), triethylamine (0.130 mL, 0.933 mmol) and N-2-pyridyl-1,2-ethanediamine (128 mg, 0.933 mmol) in DMSO (4 mL) was stirred at 100° C. for 3 hours. The reaction mixture was poured into ice water and the resulting precipitate was removed by filtration, washed with ethanol, and then dried to yield the title compound (223 mg, 82%) as a yellow solid. 1H-NMR (400 MHz, DMSO-d6) δ 1.30-1.50 (2H, m), 1.53-1.73 (1H, m), 3.01-3.12 (2H, m), 3.19-3.30 (2H, m), 3.94 (2H, s), 5.65 (1H, brs), 6.01-6.12 (2H, m), 6.29 (1H, t, J=5.5 Hz), 6.43 (2H, brs), 6.90-7.01 (1H, m), 7.52-7.60 (1H, m), 8.13 (1H, s), 14.90 (1H, s). HRESIMS (+):440.17258 (Calcd for C22H23FN5O4, 440.17341).

Workup

  1. customthe resulting precipitate was removed by filtration
  2. washwashed with ethanol
  3. customdried

Sources & evidence

ORD record
ord-f415c32b8f5542d1b0fbf9a4ff66ef81
Source dataset
uspto-grants-2014_12
Patent number
US08901112B2

Reaction notes

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