Diisopropylethylamine → HCID 25032300, compound

HRID 1175681Notes

Reaction equation

HRID 1175681 reaction equation
[CH2:1]([CH:3]1[O:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]([CH2:13][C:14]([OH:16])=O)[C:4]1=[O:17])[CH3:2].[NH2:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[CH2:24][C:23]1([C:31](=[O:32])[NH:30][C:29](=[O:33])[NH:28]1)[CH2:22]2.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[O:33]=[C:29]1[NH:28][C:23]2([CH2:22][C:21]3[C:25](=[CH:26][CH:27]=[C:19]([NH:18][C:14](=[O:16])[CH2:13][N:5]4[C:4](=[O:17])[CH:3]([CH2:1][CH3:2])[O:8][C:7]5[CH:9]=[CH:10][CH:11]=[CH:12][C:6]4=5)[CH:20]=3)[CH2:24]2)[C:31](=[O:32])[NH:30]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 184403095'-Amino-1',3'-dihydro-2H,5H-spiro[imidazolidine-4,2'-indene]-2,5-dioneHCID 53212233HCID 53212233, compound

Product 1

HCID 25032300HCID 25032300, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(2-ethyl-3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl)acetic acid (0.2 mmol, 47 mg), 5′-amino-1′,3′-dihydrospiro[imidazolidine-4,2′-indene]-2,5-dione (0.2 mmol, 43 mg) and DIPEA (0.6 mmol, 104.5 μl) in DMF (1 ml) was added HATU (0.2 mmol, 76 mg) and the reaction mixture was stirred at room temperature for 16 h. Purification by preparative reverse phase HPLC using 10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA) gave the title compound. LC/MS (10% to 99%): M/Z (M+H)+ (obs)=435.2; tR=2.71. H NMR (400 MHz, CDCl3) δ 9.39 (s, 1H), 7.68 (s, 1H), 7.48 (s, 1H), 7.24 (q, 1H), 7.03 (d, 1H), 6.87-6.92 (m, 4H), 4.65 (q, 2H), 4.41 (q, 1H), 3.34 (q, 2H), 3.00 (q, 2H), 1.78 (m, 2H), 0.94 (t, 3H).

Workup

  1. customPurification by preparative reverse phase

Sources & evidence

ORD record
ord-489bf95b260d40ec80f747ef5f5d0931
Source dataset
uspto-grants-2010_11
Patent number
US07842686B2

Reaction notes

Loading…