Diisopropylethylamine → HCID 25032384, compound

HRID 1175684Notes

Reaction equation

HRID 1175684 reaction equation
[CH2:1]([CH:5]1[S:10][C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[N:7]([CH2:15][C:16]([OH:18])=O)[C:6]1=[O:19])[CH2:2][CH2:3][CH3:4].[NH2:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[CH2:26][C:25]1([C:33](=[O:34])[NH:32][C:31](=[O:35])[NH:30]1)[CH2:24]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>[CH2:1]([CH:5]1[S:10][C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[N:7]([CH2:15][C:16]([NH:20][C:21]2[CH:22]=[C:23]3[C:27](=[CH:28][CH:29]=2)[CH2:26][C:25]2([C:33](=[O:34])[NH:32][C:31](=[O:35])[NH:30]2)[CH2:24]3)=[O:18])[C:6]1=[O:19])[CH2:2][CH2:3][CH3:4]

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 57786461HCID 57786461, compound

Product 1

HCID 25032384HCID 25032384, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(2-butyl-3-oxo-2H-benzo[b][1,4]thiazin-4(3H)-yl)acetic acid (0.2 mmol, 56 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)=479.2; tR=3.18. H NMR (400 MHz, CDCl3) δ 8.19 (s, 1H), 7.55 (d, 1H), 7.42 (q, 1H), 7.25-7.33 (m, 2H), 7.16 (d, 1H), 7.07-7.15 (m, 2H), 4.86 (d, 1H), 4.60 (d, 1H), 3.59 (t, 1H), 3.27-3.34 (m, 2H), 2.97-3.04 (m, 2H), 1.6 (m, 1H), 1.24-1.28 (m, 5H), 0.83 (t, 3H).

Workup

  1. customPurification by preparative reverse phase

Sources & evidence

ORD record
ord-34cd2a21205e4dc0af9000317c03a077
Source dataset
uspto-grants-2010_11
Patent number
US07842686B2

Reaction notes

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